NO834257L - Fremstilling av optisk aktive cyanometylestere - Google Patents

Fremstilling av optisk aktive cyanometylestere

Info

Publication number: NO834257L
Authority: NO; Norway
Prior art keywords: histidine; ketene; group; approx; cyclo
Prior art date: 1982-11-22

Application number

NO834257A

Other languages

English (en)

Norwegian (no)

Inventor

Donald W Stoutamire

Charles H Tieman

Walter Dong

Original Assignee

Shell Oil Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-11-22

Filing date

1983-11-21

Publication date

1984-05-23

1983-11-21 Application filed by Shell Oil Co filed Critical Shell Oil Co

1984-05-23 Publication of NO834257L publication Critical patent/NO834257L/no

Links

-1 CYANOMETHYL ESTERS Chemical class 0.000 title claims description 66
238000002360 preparation method Methods 0.000 title claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 92
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 87
239000003054 catalyst Substances 0.000 claims description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 53
239000002253 acid Substances 0.000 claims description 53
238000000034 method Methods 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 50
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 50
239000002904 solvent Substances 0.000 claims description 44
239000000203 mixture Substances 0.000 claims description 36
239000000047 product Substances 0.000 claims description 34
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 32
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 32
125000005843 halogen group Chemical group 0.000 claims description 31
108090000765 processed proteins & peptides Proteins 0.000 claims description 27
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 26
150000004820 halides Chemical class 0.000 claims description 24
150000001299 aldehydes Chemical class 0.000 claims description 23
125000003545 alkoxy group Chemical group 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
229910052757 nitrogen Inorganic materials 0.000 claims description 20
125000003342 alkenyl group Chemical group 0.000 claims description 19
150000002148 esters Chemical class 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical class O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 claims description 17
239000007795 chemical reaction product Substances 0.000 claims description 17
238000004519 manufacturing process Methods 0.000 claims description 16
235000001014 amino acid Nutrition 0.000 claims description 15
150000001413 amino acids Chemical class 0.000 claims description 15
OHUXOEXBXPZKPT-CHWSQXEVSA-N (2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-(1h-imidazol-5-yl)propanoic acid Chemical compound C([C@@H](N)C(=O)N[C@H](CC=1NC=NC=1)C(O)=O)C1=CC=CC=C1 OHUXOEXBXPZKPT-CHWSQXEVSA-N 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 14
150000002576 ketones Chemical class 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
LSZVSCXZSRXVOA-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbut-1-en-1-one Chemical compound CC(C)C(=C=O)C1=CC=C(Cl)C=C1 LSZVSCXZSRXVOA-UHFFFAOYSA-N 0.000 claims description 12
125000001188 haloalkyl group Chemical group 0.000 claims description 12
102000004196 processed proteins & peptides Human genes 0.000 claims description 12
150000003512 tertiary amines Chemical class 0.000 claims description 12
108010016626 Dipeptides Proteins 0.000 claims description 11
229920001184 polypeptide Polymers 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 9
125000004438 haloalkoxy group Chemical group 0.000 claims description 9
125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims description 9
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
239000012970 tertiary amine catalyst Substances 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
239000000010 aprotic solvent Substances 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
LUTLAXLNPLZCOF-UHFFFAOYSA-N 1-Methylhistidine Natural products OC(=O)C(N)(C)CC1=NC=CN1 LUTLAXLNPLZCOF-UHFFFAOYSA-N 0.000 claims description 4
BRMWTNUJHUMWMS-UHFFFAOYSA-N 3-Methylhistidine Natural products CN1C=NC(CC(N)C(O)=O)=C1 BRMWTNUJHUMWMS-UHFFFAOYSA-N 0.000 claims description 4
YIWFXZNIBQBFHR-LURJTMIESA-N Gly-His Chemical compound [NH3+]CC(=O)N[C@H](C([O-])=O)CC1=CN=CN1 YIWFXZNIBQBFHR-LURJTMIESA-N 0.000 claims description 4
JDHILDINMRGULE-LURJTMIESA-N N(pros)-methyl-L-histidine Chemical compound CN1C=NC=C1C[C@H](N)C(O)=O JDHILDINMRGULE-LURJTMIESA-N 0.000 claims description 4
BRMWTNUJHUMWMS-LURJTMIESA-N N(tele)-methyl-L-histidine Chemical compound CN1C=NC(C[C@H](N)C(O)=O)=C1 BRMWTNUJHUMWMS-LURJTMIESA-N 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 claims description 4
108010020688 glycylhistidine Proteins 0.000 claims description 4
108010085443 Anserine Proteins 0.000 claims description 3
FRJIAZKQGSCKPQ-FSPLSTOPSA-N His-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H](N)CC1=CN=CN1 FRJIAZKQGSCKPQ-FSPLSTOPSA-N 0.000 claims description 3
SLRNWACWRVGMKD-UHFFFAOYSA-N L-anserine Natural products CN1C=NC(CC(NC(=O)CCN)C(O)=O)=C1 SLRNWACWRVGMKD-UHFFFAOYSA-N 0.000 claims description 3
241000210053 Potentilla elegans Species 0.000 claims description 3
MYYIAHXIVFADCU-QMMMGPOBSA-N anserine Chemical compound CN1C=NC=C1C[C@H](NC(=O)CC[NH3+])C([O-])=O MYYIAHXIVFADCU-QMMMGPOBSA-N 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
108010040030 histidinoalanine Proteins 0.000 claims description 3
238000012546 transfer Methods 0.000 claims description 3
XRGGOHBVSVCEDQ-KBPBESRZSA-N (2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]-methylamino]-3-(1H-imidazol-5-yl)propanoic acid Chemical compound C([C@H](N(C)C(=O)[C@@H](N)CC=1C=CC=CC=1)C(O)=O)C1=CNC=N1 XRGGOHBVSVCEDQ-KBPBESRZSA-N 0.000 claims description 2
XZWXFWBHYRFLEF-FSPLSTOPSA-N Ala-His Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CN=CN1 XZWXFWBHYRFLEF-FSPLSTOPSA-N 0.000 claims description 2
SGCGMORCWLEJNZ-UWVGGRQHSA-N His-His Chemical compound C([C@H]([NH3+])C(=O)N[C@@H](CC=1NC=NC=1)C([O-])=O)C1=CN=CN1 SGCGMORCWLEJNZ-UWVGGRQHSA-N 0.000 claims description 2
LNCFUHAPNTYMJB-IUCAKERBSA-N His-Pro Chemical compound C([C@H](N)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CN=CN1 LNCFUHAPNTYMJB-IUCAKERBSA-N 0.000 claims description 2
BNQVUHQWZGTIBX-IUCAKERBSA-N Val-His Chemical compound CC(C)[C@H]([NH3+])C(=O)N[C@H](C([O-])=O)CC1=CN=CN1 BNQVUHQWZGTIBX-IUCAKERBSA-N 0.000 claims description 2
125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 2
108010070944 alanylhistidine Proteins 0.000 claims description 2
HRRYYCWYCMJNGA-ZETCQYMHSA-N alpha-methyl-L-histidine Chemical compound OC(=O)[C@](N)(C)CC1=CN=CN1 HRRYYCWYCMJNGA-ZETCQYMHSA-N 0.000 claims description 2
125000001033 ether group Chemical group 0.000 claims description 2
XAWDMXNJDWMHCN-KLXURFKVSA-N ethyl (2s)-2-amino-3-(1h-imidazol-5-yl)propanoate;dihydrochloride Chemical compound Cl.Cl.CCOC(=O)[C@@H](N)CC1=CN=CN1 XAWDMXNJDWMHCN-KLXURFKVSA-N 0.000 claims description 2
108010028295 histidylhistidine Proteins 0.000 claims description 2
108010085325 histidylproline Proteins 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
VEEIFXWJNCAVEQ-RGMNGODLSA-N methyl (2s)-2-amino-3-(1h-imidazol-5-yl)propanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CNC=N1 VEEIFXWJNCAVEQ-RGMNGODLSA-N 0.000 claims description 2
FPMLCYUEXWDCDX-WFASDCNBSA-N methyl (2s)-3-(1h-imidazol-5-yl)-2-[[(2s)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)[C@H](C)NC(=O)OCC=1C=CC=CC=1)C1=CNC=N1 FPMLCYUEXWDCDX-WFASDCNBSA-N 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims 2
NMXSWQMJOZUQKY-LBPRGKRZSA-N (2s)-2-amino-3-(1-benzylimidazol-4-yl)propanoic acid Chemical compound C1=NC(C[C@H](N)C(O)=O)=CN1CC1=CC=CC=C1 NMXSWQMJOZUQKY-LBPRGKRZSA-N 0.000 claims 1
OAXCYOTUTFGTCJ-ZETCQYMHSA-N (2s)-2-amino-3-(1-ethylimidazol-4-yl)propanoic acid Chemical compound CCN1C=NC(C[C@H](N)C(O)=O)=C1 OAXCYOTUTFGTCJ-ZETCQYMHSA-N 0.000 claims 1
ROSMBSOKFVZTHV-QMMMGPOBSA-N (2s)-2-amino-3-(1-propylimidazol-4-yl)propanoic acid Chemical compound CCCN1C=NC(C[C@H](N)C(O)=O)=C1 ROSMBSOKFVZTHV-QMMMGPOBSA-N 0.000 claims 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
XWOBNBRUDDUEEY-UHFFFAOYSA-N leucyl-histidine Chemical compound CC(C)CC(N)C(=O)NC(C(O)=O)CC1=CN=CN1 XWOBNBRUDDUEEY-UHFFFAOYSA-N 0.000 claims 1
230000001681 protective effect Effects 0.000 claims 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 39
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
239000007787 solid Substances 0.000 description 25
239000000243 solution Substances 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
125000003118 aryl group Chemical group 0.000 description 18
125000000753 cycloalkyl group Chemical group 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
239000000706 filtrate Substances 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
150000001721 carbon Chemical group 0.000 description 10
239000000126 substance Substances 0.000 description 10
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 9
150000002561 ketenes Chemical class 0.000 description 9
239000003921 oil Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
150000001335 aliphatic alkanes Chemical class 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
239000013078 crystal Substances 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 8
125000001183 hydrocarbyl group Chemical group 0.000 description 8
125000002015 acyclic group Chemical group 0.000 description 7
125000004414 alkyl thio group Chemical group 0.000 description 7
239000003708 ampul Substances 0.000 description 7
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 6
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 5
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
235000004279 alanine Nutrition 0.000 description 5
125000003710 aryl alkyl group Chemical group 0.000 description 5
125000002837 carbocyclic group Chemical group 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
239000002728 pyrethroid Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 5
VTJMSIIXXKNIDJ-SNVBAGLBSA-N (2r)-2-(4-chlorophenyl)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-SNVBAGLBSA-N 0.000 description 4
KEUPLGRNURQXAR-UHFFFAOYSA-N (4-chlorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(Cl)C=C1 KEUPLGRNURQXAR-UHFFFAOYSA-N 0.000 description 4
HMARDGYLPHOTBP-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-3-methylbut-1-en-1-one Chemical compound CC(C)C(=C=O)C1=CC=C(OC(F)F)C=C1 HMARDGYLPHOTBP-UHFFFAOYSA-N 0.000 description 4
GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000002723 alicyclic group Chemical group 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
238000009835 boiling Methods 0.000 description 4
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
238000001914 filtration Methods 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
150000007524 organic acids Chemical group 0.000 description 4
235000011007 phosphoric acid Nutrition 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000011084 recovery Methods 0.000 description 4
238000000926 separation method Methods 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
LLMLSUSAKZVFOA-NJGYIYPDSA-N (1r,3r)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(O)=O LLMLSUSAKZVFOA-NJGYIYPDSA-N 0.000 description 3
JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 3
BWPYAVCZZUTOBY-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutanoyl chloride Chemical compound CC(C)C(C(Cl)=O)C1=CC=C(Cl)C=C1 BWPYAVCZZUTOBY-UHFFFAOYSA-N 0.000 description 3
VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000287828 Gallus gallus Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
125000004391 aryl sulfonyl group Chemical group 0.000 description 3
125000005110 aryl thio group Chemical group 0.000 description 3
125000004104 aryloxy group Chemical group 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000499 gel Substances 0.000 description 3
125000000262 haloalkenyl group Chemical group 0.000 description 3
125000004995 haloalkylthio group Chemical group 0.000 description 3
125000001072 heteroaryl group Chemical group 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
239000003444 phase transfer catalyst Substances 0.000 description 3
229920000768 polyamine Polymers 0.000 description 3
239000000376 reactant Substances 0.000 description 3
125000006413 ring segment Chemical group 0.000 description 3
150000005199 trimethylbenzenes Chemical class 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
GXNAZXKPZSMSJC-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-3-methylbutanoyl chloride Chemical compound CC(C)C(C(Cl)=O)C1=CC=C(OC(F)F)C=C1 GXNAZXKPZSMSJC-UHFFFAOYSA-N 0.000 description 2
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 2
LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000003158 alcohol group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
239000003849 aromatic solvent Substances 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
150000001934 cyclohexanes Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000002390 heteroarenes Chemical class 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 2
108010092114 histidylphenylalanine Proteins 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
YGPSJZOEDVAXAB-UHFFFAOYSA-N kynurenine Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC=C1N YGPSJZOEDVAXAB-UHFFFAOYSA-N 0.000 description 2
239000000155 melt Substances 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
VEEIFXWJNCAVEQ-FYZOBXCZSA-N methyl (2r)-2-amino-3-(1h-imidazol-5-yl)propanoate;hydrochloride Chemical compound Cl.COC(=O)[C@H](N)CC1=CNC=N1 VEEIFXWJNCAVEQ-FYZOBXCZSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical class CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
235000008729 phenylalanine Nutrition 0.000 description 2
150000003016 phosphoric acids Chemical class 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
238000002390 rotary evaporation Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
238000001308 synthesis method Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
CYCYDSJDZNVSPP-OVEKKEMJSA-N (1r,3s)-3-(1,2-dibromo-2,2-dichloroethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C(Br)C(Cl)(Cl)Br)[C@H]1C(O)=O CYCYDSJDZNVSPP-OVEKKEMJSA-N 0.000 description 1
RRONHWAVOYADJL-OAHLLOKOSA-N (2r)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 RRONHWAVOYADJL-OAHLLOKOSA-N 0.000 description 1
FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
PADSRMKFROZNET-UHFFFAOYSA-N 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carbonyl chloride Chemical compound C1=CC(OCC)=CC=C1C1(C(Cl)=O)C(Cl)(Cl)C1 PADSRMKFROZNET-UHFFFAOYSA-N 0.000 description 1
VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 description 1
UQLRMDQICPNIIJ-UHFFFAOYSA-N 2-(carbamoylamino)-3-hydroxypropanoic acid Chemical compound NC(=O)NC(CO)C(O)=O UQLRMDQICPNIIJ-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
VMEHOTODTPXCKT-UHFFFAOYSA-N 2-hydroxy-2-methylbutanenitrile Chemical compound CCC(C)(O)C#N VMEHOTODTPXCKT-UHFFFAOYSA-N 0.000 description 1
NGLPDXCYIUHTNP-UHFFFAOYSA-N 2-hydroxy-2-phenylpropanenitrile Chemical compound N#CC(O)(C)C1=CC=CC=C1 NGLPDXCYIUHTNP-UHFFFAOYSA-N 0.000 description 1
102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 1
JIIXEQFJRLRHSW-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C=C(Br)Br)C1C(Cl)=O JIIXEQFJRLRHSW-UHFFFAOYSA-N 0.000 description 1
OXCVCJVUOYADBS-UHFFFAOYSA-N 3-methylbut-1-en-1-one Chemical compound CC(C)C=C=O OXCVCJVUOYADBS-UHFFFAOYSA-N 0.000 description 1
JDICMOLUAHZVDS-UHFFFAOYSA-N 4-fluoro-3-phenoxybenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1OC1=CC=CC=C1 JDICMOLUAHZVDS-UHFFFAOYSA-N 0.000 description 1
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
YPWSLBHSMIKTPR-UHFFFAOYSA-N Cystathionine Natural products OC(=O)C(N)CCSSCC(N)C(O)=O YPWSLBHSMIKTPR-UHFFFAOYSA-N 0.000 description 1
ILRYLPWNYFXEMH-UHFFFAOYSA-N D-cystathionine Natural products OC(=O)C(N)CCSCC(N)C(O)=O ILRYLPWNYFXEMH-UHFFFAOYSA-N 0.000 description 1
COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 1
229930182832 D-phenylalanine Natural products 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
XMAUFHMAAVTODF-STQMWFEESA-N His-Phe Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CN=CN1 XMAUFHMAAVTODF-STQMWFEESA-N 0.000 description 1
101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 1
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
ZQISRDCJNBUVMM-UHFFFAOYSA-N L-Histidinol Natural products OCC(N)CC1=CN=CN1 ZQISRDCJNBUVMM-UHFFFAOYSA-N 0.000 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
FSBIGDSBMBYOPN-VKHMYHEASA-N L-canavanine Chemical compound OC(=O)[C@@H](N)CCONC(N)=N FSBIGDSBMBYOPN-VKHMYHEASA-N 0.000 description 1
RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
ILRYLPWNYFXEMH-WHFBIAKZSA-N L-cystathionine Chemical compound [O-]C(=O)[C@@H]([NH3+])CCSC[C@H]([NH3+])C([O-])=O ILRYLPWNYFXEMH-WHFBIAKZSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
ZQISRDCJNBUVMM-YFKPBYRVSA-N L-histidinol Chemical compound OC[C@@H](N)CC1=CNC=N1 ZQISRDCJNBUVMM-YFKPBYRVSA-N 0.000 description 1
WZNJWVWKTVETCG-YFKPBYRVSA-N L-mimosine Chemical compound OC(=O)[C@@H](N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-YFKPBYRVSA-N 0.000 description 1
RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
FSBIGDSBMBYOPN-UHFFFAOYSA-N O-guanidino-DL-homoserine Natural products OC(=O)C(N)CCON=C(N)N FSBIGDSBMBYOPN-UHFFFAOYSA-N 0.000 description 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
XEXSSIBQYNKFBX-KBPBESRZSA-N Phe-Gly-His Chemical compound C([C@H](N)C(=O)NCC(=O)N[C@@H](CC=1N=CNC=1)C(O)=O)C1=CC=CC=C1 XEXSSIBQYNKFBX-KBPBESRZSA-N 0.000 description 1
QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
229920002873 Polyethylenimine Polymers 0.000 description 1
LKHMSUATUYVXSQ-UHFFFAOYSA-N [2-(4-nitrophenyl)acetyl] 2-(4-nitrophenyl)acetate Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC(=O)OC(=O)CC1=CC=C([N+]([O-])=O)C=C1 LKHMSUATUYVXSQ-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001294 alanine derivatives Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
CSQVURORVZDRAL-UHFFFAOYSA-N benzyl n-(1-chloro-3-methyl-1-oxobutan-2-yl)-n-[3-chloro-4-(trifluoromethyl)phenyl]carbamate Chemical compound C=1C=C(C(F)(F)F)C(Cl)=CC=1N(C(C(C)C)C(Cl)=O)C(=O)OCC1=CC=CC=C1 CSQVURORVZDRAL-UHFFFAOYSA-N 0.000 description 1
CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
229910052729 chemical element Inorganic materials 0.000 description 1
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
KMPWYEUPVWOPIM-LSOMNZGLSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@H]3N4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-LSOMNZGLSA-N 0.000 description 1
MDIQXIJPQWLFSD-NJGYIYPDSA-N cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(O)=O MDIQXIJPQWLFSD-NJGYIYPDSA-N 0.000 description 1
235000013477 citrulline Nutrition 0.000 description 1
229960002173 citrulline Drugs 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
RMKNCYHVESPYFD-UHFFFAOYSA-N decan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCC[NH3+] RMKNCYHVESPYFD-UHFFFAOYSA-N 0.000 description 1
VGBHJWFEBLBTHG-UHFFFAOYSA-M decyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCC)C1=CC=CC=C1 VGBHJWFEBLBTHG-UHFFFAOYSA-M 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
ZXSBWHUKLNLVIR-UHFFFAOYSA-M ethyl(trioctyl)azanium;bromide Chemical compound [Br-].CCCCCCCC[N+](CC)(CCCCCCCC)CCCCCCCC ZXSBWHUKLNLVIR-UHFFFAOYSA-M 0.000 description 1
238000006200 ethylation reaction Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000005189 flocculation Methods 0.000 description 1
230000016615 flocculation Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002410 histidine derivatives Chemical group 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
229950002289 mimosine Drugs 0.000 description 1
BOMZLGWYAKKMPG-UHFFFAOYSA-N n-(6-aminohexyl)-n-prop-2-enoylprop-2-enamide Chemical compound NCCCCCCN(C(=O)C=C)C(=O)C=C BOMZLGWYAKKMPG-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical group 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000005501 phase interface Effects 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
RPVDAUDBFGUPKL-UHFFFAOYSA-N propan-2-yl 2-(4-chlorophenyl)acetate Chemical compound CC(C)OC(=O)CC1=CC=C(Cl)C=C1 RPVDAUDBFGUPKL-UHFFFAOYSA-N 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
230000006340 racemization Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000012360 testing method Methods 0.000 description 1
BIMIJXSZMVGEJR-UHFFFAOYSA-M tetra(nonyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCC[N+](CCCCCCCCC)(CCCCCCCCC)CCCCCCCCC BIMIJXSZMVGEJR-UHFFFAOYSA-M 0.000 description 1
IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
KCSOHLKZTZMKQA-UHFFFAOYSA-M tetraheptylazanium;iodide Chemical compound [I-].CCCCCCC[N+](CCCCCCC)(CCCCCCC)CCCCCCC KCSOHLKZTZMKQA-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
UJMLRSWRUXXZEW-UHFFFAOYSA-M tributyl(octyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CCCC)(CCCC)CCCC UJMLRSWRUXXZEW-UHFFFAOYSA-M 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/23—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/87—Preparation of ketenes or dimeric ketenes
- C07C45/89—Preparation of ketenes or dimeric ketenes from carboxylic acids, their anhydrides, esters or halides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/88—Ketenes; Dimeric ketenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06147—Dipeptides with the first amino acid being heterocyclic and His-amino acid; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Biochemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Toxicology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Peptides Or Proteins (AREA)

NO834257A 1982-11-22 1983-11-21 Fremstilling av optisk aktive cyanometylestere NO834257L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US44376482A	1982-11-22	1982-11-22
US44351382A	1982-11-22	1982-11-22
US44376382A	1982-11-22	1982-11-22

Publications (1)

Publication Number	Publication Date
NO834257L true NO834257L (no)	1984-05-23

Family

ID=27412181

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO834257A NO834257L (no)	1982-11-22	1983-11-21	Fremstilling av optisk aktive cyanometylestere

Country Status (24)

Country	Link
EP (2)	EP0109681B1 (ja)
JP (2)	JPH02270852A (ja)
KR (1)	KR890003660B1 (ja)
AU (1)	AU577032B2 (ja)
BG (1)	BG40805A3 (ja)
BR (1)	BR8306312A (ja)
CA (1)	CA1263800A (ja)
DD (1)	DD216453A5 (ja)
DE (1)	DE3382524D1 (ja)
DK (1)	DK532383A (ja)
ES (1)	ES8601860A1 (ja)
FI (1)	FI834259A7 (ja)
GR (1)	GR79041B (ja)
HU (1)	HU200584B (ja)
IL (1)	IL70155A (ja)
IN (1)	IN161692B (ja)
MX (1)	MX167266B (ja)
NO (1)	NO834257L (ja)
NZ (1)	NZ206106A (ja)
OA (1)	OA07593A (ja)
PL (1)	PL244585A1 (ja)
PT (1)	PT77685B (ja)
SU (1)	SU1542412A3 (ja)
YU (2)	YU43197B (ja)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU576322B2 (en) *	1983-07-22	1988-08-25	Ici Australia Limited	Alpha-substituted-alpha-cyanomethyl alcohols
US4554102A (en) *	1983-09-26	1985-11-19	Shell Oil Company	Cyanohydrination catalyst comprising non-crystalline or amorphous dipeptide
EP0172380A3 (en) *	1984-08-20	1987-06-16	E.I. Du Pont De Nemours And Company	Preparation of cyanomethyl esters
US4611077A (en) *	1985-06-26	1986-09-09	Shell Oil Company	Increasing enantiomeric selectivity in chiral cyanohydrination
US4611076A (en) *	1985-06-26	1986-09-09	Shell Oil Company	Chiral cyanohydrination process
JPH064578B2 (ja) *	1986-12-15	1994-01-19	鐘淵化学工業株式会社	光学活性シアノ化合物の製造方法
JP2924000B2 (ja) *	1989-09-29	1999-07-26	住友化学工業株式会社	不斉誘起触媒
CA2062233A1 (en) *	1991-03-12	1992-09-13	Atsunori Mori	Catalyst for asymmetric induction
GB0304132D0 (en) *	2003-02-24	2003-03-26	Syngenta Ltd	Chemical process
NZ600755A (en) *	2009-12-25	2014-10-31	Suntory Holdings Ltd	Learning motivation improvers

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2383137A (en) *	1939-12-05	1945-08-21	American Cyanamid Co	Acetylation of cyanohydrins
BE635217A (ja) *	1963-07-22
ZA7911B (en) *	1978-01-31	1980-01-30	Roussel Uclaf	Optically-active substituted benzyl alcohol and process for preparing it
FR2458542A1 (fr) *	1979-06-12	1981-01-02	Roussel Uclaf	Procede de preparation d'alcools a-cyanes optiquement actifs
DE3116474A1 (de) *	1981-04-25	1982-11-11	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von optisch aktiven carbonsaeuren
JPS5829757A (ja) *	1981-08-17	1983-02-22	Nippon Kayaku Co Ltd	光学活性マンデロニトリルの製造法
AU527142B2 (en) *	1981-12-16	1983-02-17	Bayer Aktiengesellschaft	Phenoxy benzyl alcohols
ZA837994B (en) *	1982-11-22	1984-06-27	Shell Oil Co	Process for the preparation of optically-active cyanomethyl esters
AU576322B2 (en) *	1983-07-22	1988-08-25	Ici Australia Limited	Alpha-substituted-alpha-cyanomethyl alcohols

1983
- 1983-10-31 NZ NZ206106A patent/NZ206106A/en unknown
- 1983-11-02 IN IN1346/CAL/83A patent/IN161692B/en unknown
- 1983-11-07 IL IL70155A patent/IL70155A/xx not_active IP Right Cessation
- 1983-11-11 YU YU2227/83A patent/YU43197B/xx unknown
- 1983-11-11 MX MX199385A patent/MX167266B/es unknown
- 1983-11-16 PL PL24458583A patent/PL244585A1/xx unknown
- 1983-11-17 BR BR8306312A patent/BR8306312A/pt not_active IP Right Cessation
- 1983-11-17 DD DD83256815A patent/DD216453A5/de unknown
- 1983-11-18 EP EP83111562A patent/EP0109681B1/en not_active Expired - Lifetime
- 1983-11-18 PT PT77685A patent/PT77685B/pt unknown
- 1983-11-18 EP EP91201451A patent/EP0451927A1/en not_active Withdrawn
- 1983-11-18 DE DE8383111562T patent/DE3382524D1/de not_active Expired - Lifetime
- 1983-11-21 SU SU833675006A patent/SU1542412A3/ru active
- 1983-11-21 ES ES527417A patent/ES8601860A1/es not_active Expired
- 1983-11-21 CA CA000441540A patent/CA1263800A/en not_active Expired
- 1983-11-21 DK DK532383A patent/DK532383A/da not_active Application Discontinuation
- 1983-11-21 AU AU21555/83A patent/AU577032B2/en not_active Ceased
- 1983-11-21 HU HU834003A patent/HU200584B/hu not_active IP Right Cessation
- 1983-11-21 NO NO834257A patent/NO834257L/no unknown
- 1983-11-21 FI FI834259A patent/FI834259A7/fi not_active Application Discontinuation
- 1983-11-22 KR KR1019830005527A patent/KR890003660B1/ko not_active Expired
- 1983-11-22 BG BG063151A patent/BG40805A3/xx unknown
- 1983-11-22 OA OA58163A patent/OA07593A/xx unknown
- 1983-11-22 GR GR73016A patent/GR79041B/el unknown
1986
- 1986-03-12 YU YU369/86A patent/YU43429B/xx unknown
1989
- 1989-11-22 JP JP1302306A patent/JPH02270852A/ja active Pending
1990
- 1990-06-25 JP JP2164329A patent/JPH03238053A/ja active Pending

Also Published As

Publication number	Publication date
DK532383A (da)	1984-05-23
PL244585A1 (en)	1985-11-05
PT77685A (en)	1983-12-01
ES527417A0 (es)	1985-11-01
OA07593A (en)	1985-03-31
YU36986A (en)	1986-12-31
FI834259A7 (fi)	1984-05-23
AU2155583A (en)	1984-05-31
IN161692B (ja)	1988-01-16
KR890003660B1 (ko)	1989-09-29
ES8601860A1 (es)	1985-11-01
EP0109681A2 (en)	1984-05-30
CA1263800A (en)	1989-12-05
GR79041B (ja)	1984-10-02
IL70155A0 (en)	1984-02-29
PT77685B (en)	1986-03-27
BG40805A3 (bg)	1987-02-16
EP0109681A3 (en)	1986-01-15
IL70155A (en)	1989-09-10
KR840007715A (ko)	1984-12-20
DD216453A5 (de)	1984-12-12
BR8306312A (pt)	1984-07-03
YU43197B (en)	1989-04-30
YU222783A (en)	1986-12-31
YU43429B (en)	1989-06-30
EP0451927A1 (en)	1991-10-16
MX167266B (es)	1993-03-12
HU200584B (en)	1990-07-28
NZ206106A (en)	1987-10-30
FI834259A0 (fi)	1983-11-21
DK532383D0 (da)	1983-11-21
EP0109681B1 (en)	1992-03-11
SU1542412A3 (ru)	1990-02-07
HUT37915A (en)	1986-03-28
JPH02270852A (ja)	1990-11-05
AU577032B2 (en)	1988-09-15
DE3382524D1 (de)	1992-04-16
JPH03238053A (ja)	1991-10-23

Publication	Publication Date	Title
Seebach et al.	1985	α‐Alkylation of Amino Acids without Racemization. Preparation of Either (S)‐or (R)‐α‐Methyldopa from (S)‐Alanine
KR890003660B1 (ko)	1989-09-29	광학적 활성인 시아노메틸에스테르의 제조방법
JPS59116256A (ja)	1984-07-05	Ｓ―α―シアノ―３―フェノキシベンジルアルコール類の製造方法
US4529810A (en)	1985-07-16	Preparation of optically-active alpha-substituted carboxylic esters and acids
US3996246A (en)	1976-12-07	Resolution of racemic pantolactone
US4560515A (en)	1985-12-24	Preparation of optically-active cyanomethyl esters
CA1246588A (en)	1988-12-13	Process for preparing substituted oxazolines
US4723027A (en)	1988-02-02	Preparation of optically active alpha-hydroxynitriles
EP0291626A2 (en)	1988-11-23	Process for the preparation of optically-active cyanomethyl esters
Cativiela et al.	1985	On the synthesis of geometric isomers of 2‐methyl (or phenyl)‐4‐[α‐arylethylidene]‐5 (4H)‐oxazolones
US4570017A (en)	1986-02-11	Preparation of optically-active (mixed) anhydrides and acids
EP0312124A2 (en)	1989-04-19	Process for the preparation of optically-active cyanomethyl esters
US4330484A (en)	1982-05-18	Diastereomeric salts of malic acid and 2-aminobutanol, and process for the resolution of rademis maic acid
FI97054C (fi)	1996-10-10	Menetelmä karboksyylihappojen talteenottamiseksi niiden vesipitoisista liuoksista
HU189456B (en)	1986-07-28	Process for preparing new methyl esters of substituted cyclopropane carboxylic acids
Biava et al.	2013	Obtention of enantiomerically pure 5, 5, 5-trifluoro-L-isoleucine and 5, 5, 5-trifluoro-L-alloisoleucine
JPS6054952B2 (ja)	1985-12-03	シアノ置換エステルの製造方法
Juaristi et al.	1995	Highly Diastereoselective Alkylation of 1-Benzoyl-2-alkyl-3-(1'-methylbenzyl) imidazolidin-4-ones
US4546198A (en)	1985-10-08	Asymmetric synthesis of esters and acids
US4094904A (en)	1978-06-13	Process of racemizing an optically active phenyl glycine amide with or without a substituted phenyl group
TW200418389A (en)	2004-10-01	Chemical process
Yasuhara et al.	1978	Use of shift reagent with MTPA derivatives in 1H NMR spectroscopy. IV. Determination of absolute configuration and enantiomeric purity of amino acid derivatives.
Lidor et al.	1997	A facile synthesis for racemic and optically active 1-aminoindans
JPS59163344A (ja)	1984-09-14	光学活性アルフア置換カルボン酸またはエステルの製法
US4582646A (en)	1986-04-15	Preparation of cyanomethyl esters