CA1089470A - Composes a base d'oxazolidine - Google Patents

Composes a base d'oxazolidine

Info

Publication number: CA1089470A
Authority: CA; Canada
Prior art keywords: cob; acyl; yield; acid; oxa
Prior art date: 1977-04-28
Legal status (The legal status 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 status listed.): Expired

Application number

CA340,710A

Other languages

English (en)

Inventor

Mitsuru Yoshioka

Teruji Tsuji

Yasuhiro Nishitani

Wataru Nagata

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shionogi and Co Ltd

Original Assignee

Shionogi and Co Ltd

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.)

1977-04-28

Filing date

1979-11-27

Publication date

1980-11-11

1977-04-28 Priority claimed from CA277,296A external-priority patent/CA1087194A/fr

1979-11-27 Application filed by Shionogi and Co Ltd filed Critical Shionogi and Co Ltd

1979-11-27 Priority to CA340,710A priority Critical patent/CA1089470A/fr

1980-11-11 Application granted granted Critical

1980-11-11 Publication of CA1089470A publication Critical patent/CA1089470A/fr

Status Expired legal-status Critical Current

Links

150000002917 oxazolidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 61
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 58
-1 diphenylmethoxycarbonyl Chemical group 0.000 claims description 297
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 30
238000000034 method Methods 0.000 claims description 28
230000008569 process Effects 0.000 claims description 19
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 18
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 12
238000003786 synthesis reaction Methods 0.000 abstract description 9
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract description 8
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract description 5
239000000543 intermediate Substances 0.000 abstract description 5
230000000707 stereoselective effect Effects 0.000 abstract description 2
239000003242 anti bacterial agent Substances 0.000 abstract 1
229940088710 antibiotic agent Drugs 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 99
229910001868 water Inorganic materials 0.000 description 96
125000002252 acyl group Chemical group 0.000 description 95
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 93
238000006243 chemical reaction Methods 0.000 description 83
239000000203 mixture Substances 0.000 description 83
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
239000000243 solution Substances 0.000 description 74
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 71
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 69
239000000460 chlorine Substances 0.000 description 69
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 63
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 55
239000002253 acid Substances 0.000 description 46
230000002829 reductive effect Effects 0.000 description 45
239000003153 chemical reaction reagent Substances 0.000 description 43
229940093499 ethyl acetate Drugs 0.000 description 35
235000019439 ethyl acetate Nutrition 0.000 description 35
125000000217 alkyl group Chemical group 0.000 description 33
239000001257 hydrogen Substances 0.000 description 31
229910052739 hydrogen Inorganic materials 0.000 description 31
238000001816 cooling Methods 0.000 description 30
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 29
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
229940073584 methylene chloride Drugs 0.000 description 25
239000002904 solvent Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
229910052736 halogen Inorganic materials 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 23
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
150000002367 halogens Chemical class 0.000 description 22
150000002576 ketones Chemical class 0.000 description 22
239000007864 aqueous solution Substances 0.000 description 21
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
229940022663 acetate Drugs 0.000 description 19
229910052801 chlorine Inorganic materials 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 18
229960000583 acetic acid Drugs 0.000 description 18
230000000269 nucleophilic effect Effects 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
229960003010 sodium sulfate Drugs 0.000 description 17
229910052938 sodium sulfate Inorganic materials 0.000 description 17
235000011152 sodium sulphate Nutrition 0.000 description 17
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
238000004587 chromatography analysis Methods 0.000 description 15
150000002148 esters Chemical class 0.000 description 15
150000003839 salts Chemical class 0.000 description 15
239000007858 starting material Substances 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
150000001408 amides Chemical class 0.000 description 14
XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 14
229960003390 magnesium sulfate Drugs 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
230000009467 reduction Effects 0.000 description 14
238000006722 reduction reaction Methods 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
125000003710 aryl alkyl group Chemical group 0.000 description 13
229910052751 metal Inorganic materials 0.000 description 13
239000002184 metal Substances 0.000 description 13
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 12
239000004411 aluminium Substances 0.000 description 12
229910052782 aluminium Inorganic materials 0.000 description 12
235000010210 aluminium Nutrition 0.000 description 12
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
229910000041 hydrogen chloride Inorganic materials 0.000 description 12
229910000761 Aluminium amalgam Inorganic materials 0.000 description 11
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 11
125000003118 aryl group Chemical group 0.000 description 11
150000004820 halides Chemical class 0.000 description 11
150000002431 hydrogen Chemical group 0.000 description 11
239000005457 ice water Substances 0.000 description 11
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
150000005826 halohydrocarbons Chemical class 0.000 description 10
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 9
230000002140 halogenating effect Effects 0.000 description 9
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
125000004423 acyloxy group Chemical group 0.000 description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 8
239000012043 crude product Substances 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
229940086542 triethylamine Drugs 0.000 description 8
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000011701 zinc Substances 0.000 description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
229960000443 hydrochloric acid Drugs 0.000 description 6
229910052742 iron Inorganic materials 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
229910052725 zinc Inorganic materials 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
101150041968 CDC13 gene Proteins 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
125000003435 aroyl group Chemical group 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
150000004678 hydrides Chemical class 0.000 description 5
235000011167 hydrochloric acid Nutrition 0.000 description 5
125000004356 hydroxy functional group Chemical group O* 0.000 description 5
229910052500 inorganic mineral Inorganic materials 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
235000001055 magnesium Nutrition 0.000 description 5
229940091250 magnesium supplement Drugs 0.000 description 5
229960002523 mercuric chloride Drugs 0.000 description 5
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
239000011707 mineral Substances 0.000 description 5
229910052759 nickel Inorganic materials 0.000 description 5
150000002902 organometallic compounds Chemical class 0.000 description 5
229960003975 potassium Drugs 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000000126 substance Substances 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
235000016804 zinc Nutrition 0.000 description 5
CUMWTOXZSYWDEB-UHFFFAOYSA-N 1-(2-oxopropyl)azetidin-2-one Chemical compound CC(=O)CN1CCC1=O CUMWTOXZSYWDEB-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
229910000497 Amalgam Inorganic materials 0.000 description 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical compound O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 description 4
229930182555 Penicillin Natural products 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
229910008066 SnC12 Inorganic materials 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
150000002960 penicillins Chemical class 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 4
239000011592 zinc chloride Substances 0.000 description 4
235000005074 zinc chloride Nutrition 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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 description 3
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
230000009471 action Effects 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
150000001342 alkaline earth metals Chemical class 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
150000001728 carbonyl compounds Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
239000003759 ester based solvent Substances 0.000 description 3
238000005755 formation reaction Methods 0.000 description 3
125000005283 haloketone group Chemical group 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000006501 nitrophenyl group Chemical group 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
125000002524 organometallic group Chemical group 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
229910052718 tin Inorganic materials 0.000 description 3
239000011135 tin Substances 0.000 description 3
125000003944 tolyl group Chemical group 0.000 description 3
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
229910052721 tungsten Inorganic materials 0.000 description 3
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
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239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229940083542 sodium Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
JNQGCYCJQVDZFV-UHFFFAOYSA-M sodium;2-oxo-2-phenylmethoxyacetate Chemical compound [Na+].[O-]C(=O)C(=O)OCC1=CC=CC=C1 JNQGCYCJQVDZFV-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
241000894007 species Species 0.000 description 1
229940013123 stannous chloride Drugs 0.000 description 1
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
150000008054 sulfonate salts Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical group CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229960001763 zinc sulfate Drugs 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA340,710A 1977-04-28 1979-11-27 Composes a base d'oxazolidine Expired CA1089470A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA340,710A CA1089470A (fr)	1977-04-28	1979-11-27	Composes a base d'oxazolidine

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA277,296A CA1087194A (fr)	1977-04-28	1977-04-28	Composes a base d'oxazolidine
CA340,710A CA1089470A (fr)	1977-04-28	1979-11-27	Composes a base d'oxazolidine

Publications (1)

Publication Number	Publication Date
CA1089470A true CA1089470A (fr)	1980-11-11

Family

ID=25668503

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA340,710A Expired CA1089470A (fr)	1977-04-28	1979-11-27	Composes a base d'oxazolidine

Country Status (1)

Country	Link
CA (1)	CA1089470A (fr)

1979
- 1979-11-27 CA CA340,710A patent/CA1089470A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-11-12	MKEX	Expiry

Publication	Publication Date	Title
CA1132547A (fr)	1982-09-28	Cyclisation pour former des noyaux cephem et leurs intermediaires
US4159984A (en)	1979-07-03	Reductive cleavage of oxazolidine compounds
EP0037592A2 (fr)	1981-10-14	Composés contenant le groupement bêta-lactame
US4366316A (en)	1982-12-28	1-Oxadethiacepham compounds and process for producing said compounds
US4060688A (en)	1977-11-29	Cephalosporin intermediates
US4122262A (en)	1978-10-24	Intermediates and methods for preparing 7-acylamino-8-oxo-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid derivatives
US4296236A (en)	1981-10-20	7-(or 6-) Substituted-7-(or 6-)acylimino cephalosporin (or penicillin) compounds
US4031084A (en)	1977-06-21	Process for cephalosporin antibiotic intermediates
US4166816A (en)	1979-09-04	Methods and intermediates for preparing cis-4-oxoazetidine intermediates
CA1070688A (fr)	1980-01-29	Analogues des cephalosporines
CA1089469A (fr)	1980-11-11	Composes d'oxazolidine
US4072674A (en)	1978-02-07	Cis-4-oxoazetidine intermediates and methods of preparing them
CA1087194A (fr)	1980-10-07	Composes a base d'oxazolidine
CA1089476A (fr)	1980-11-11	Clivage par reduction de l'oxazolidine
US4008230A (en)	1977-02-15	Process for preparing 3-hydroxy cephalosporins
US4048162A (en)	1977-09-13	Process for preparing 3-hydroxy cephalosporins
JPH04225985A (ja)	1992-08-14	セフアロスポリン化合物
US4675396A (en)	1987-06-23	7-Oxo-4-thia-1-azabicyclo(3,2,0)heptane derivatives
US4604460A (en)	1986-08-05	1-oxadethiacepham compounds
KR870000528B1 (ko)	1987-03-14	3-아지도 세팔로스포린의 제조방법
US4079179A (en)	1978-03-14	6-Loweralkoxy or loweralkylthio-3-cephem-4-carboxylic acids
US4284766A (en)	1981-08-18	Process for the preparation of cephalosporin compounds
EP0096496B1 (fr)	1986-07-23	Procédé de préparation de composés de la pénicilline et de la céphalosporine et produits intermédiaires pour ce procédé
US4478997A (en)	1984-10-23	1-Oxadethiacepham compounds
AU618624B2 (en)	1992-01-02	Process for 1-carba(dethia)cephalosporins