CA1318917C - Procede pour la preparation d'acides ó-arylalcanoiques optiquement actifs, et nouveaux intermediaires de ceux-ci - Google Patents

Procede pour la preparation d'acides ó-arylalcanoiques optiquement actifs, et nouveaux intermediaires de ceux-ci

Info

Publication number: CA1318917C
Authority: CA; Canada
Prior art keywords: acid; methoxy; naphthyl; mixture; bromo
Prior art date: 1984-04-06
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 - Fee Related

Application number

CA000614747A

Other languages

English (en)

Inventor

Fulvio Uggeri

Silvia Cavicchioli

Claudio Giordano

Graziano Castaldi

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.)

Zambon SpA

Original Assignee

Zambon SpA

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.)

1984-04-06

Filing date

1989-09-29

Publication date

1993-06-08

1984-08-06 Priority claimed from IT07206/84A external-priority patent/IT1199447B/it

1984-08-06 Priority claimed from IT8407207A external-priority patent/IT1207420B/it

1985-04-04 Priority claimed from CA000478585A external-priority patent/CA1282410C/fr

1989-09-29 Application filed by Zambon SpA filed Critical Zambon SpA

1989-09-29 Priority to CA000614747A priority Critical patent/CA1318917C/fr

1993-06-08 Application granted granted Critical

1993-06-08 Publication of CA1318917C publication Critical patent/CA1318917C/fr

2010-06-08 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 97
150000007513 acids Chemical class 0.000 title claims abstract description 36
239000000543 intermediate Substances 0.000 title abstract description 5
238000002360 preparation method Methods 0.000 title description 65
238000000034 method Methods 0.000 title description 40
125000003118 aryl group Chemical group 0.000 claims abstract description 32
150000002148 esters Chemical class 0.000 claims abstract description 31
-1 phenoxy, thienylcarbonyl Chemical group 0.000 claims abstract description 26
229910052794 bromium Inorganic materials 0.000 claims abstract description 24
229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
229910052740 iodine Inorganic materials 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
229910052751 metal Inorganic materials 0.000 claims abstract description 11
239000002184 metal Substances 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
150000001768 cations Chemical class 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
125000006686 (C1-C24) alkyl group Chemical group 0.000 claims abstract 3
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract 2
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
229910052783 alkali metal Inorganic materials 0.000 claims abstract 2
125000004414 alkyl thio group Chemical group 0.000 claims abstract 2
125000003367 polycyclic group Chemical group 0.000 claims abstract 2
239000000460 chlorine Substances 0.000 claims description 19
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 abstract description 5
150000001340 alkali metals Chemical class 0.000 abstract 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
229910052760 oxygen Inorganic materials 0.000 abstract 1
239000001301 oxygen Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 118
239000000203 mixture Substances 0.000 description 104
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 91
239000000243 solution Substances 0.000 description 84
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 74
238000005160 1H NMR spectroscopy Methods 0.000 description 62
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 59
239000011541 reaction mixture Substances 0.000 description 56
239000002904 solvent Substances 0.000 description 56
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 50
238000003756 stirring Methods 0.000 description 44
150000001875 compounds Chemical class 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
229960004132 diethyl ether Drugs 0.000 description 37
238000004128 high performance liquid chromatography Methods 0.000 description 37
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 32
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
239000012074 organic phase Substances 0.000 description 27
239000007864 aqueous solution Substances 0.000 description 26
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
230000008707 rearrangement Effects 0.000 description 24
239000000284 extract Substances 0.000 description 22
239000000047 product Substances 0.000 description 21
229940095574 propionic acid Drugs 0.000 description 21
CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 20
239000000741 silica gel Substances 0.000 description 20
229910002027 silica gel Inorganic materials 0.000 description 20
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 19
239000003480 eluent Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
229910052938 sodium sulfate Inorganic materials 0.000 description 18
235000011152 sodium sulphate Nutrition 0.000 description 18
229910052799 carbon Inorganic materials 0.000 description 16
238000001704 evaporation Methods 0.000 description 16
229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
238000005658 halogenation reaction Methods 0.000 description 15
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 15
230000003287 optical effect Effects 0.000 description 15
235000017557 sodium bicarbonate Nutrition 0.000 description 15
239000008346 aqueous phase Substances 0.000 description 14
229960002009 naproxen Drugs 0.000 description 14
229910000402 monopotassium phosphate Inorganic materials 0.000 description 13
239000011975 tartaric acid Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
101150041968 CDC13 gene Proteins 0.000 description 12
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000004458 analytical method Methods 0.000 description 12
230000000875 corresponding effect Effects 0.000 description 12
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
239000012298 atmosphere Substances 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
229940073584 methylene chloride Drugs 0.000 description 11
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
230000026030 halogenation Effects 0.000 description 10
238000000746 purification Methods 0.000 description 10
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 9
229910000029 sodium carbonate Inorganic materials 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
150000001721 carbon Chemical group 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
230000014759 maintenance of location Effects 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
230000000707 stereoselective effect Effects 0.000 description 8
235000002906 tartaric acid Nutrition 0.000 description 8
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
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 7
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
150000004702 methyl esters Chemical class 0.000 description 7
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
235000019260 propionic acid Nutrition 0.000 description 6
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
LNBHUCHAFZUEGJ-UHFFFAOYSA-N europium(3+) Chemical compound [Eu+3] LNBHUCHAFZUEGJ-UHFFFAOYSA-N 0.000 description 5
239000000499 gel Substances 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000010992 reflux Methods 0.000 description 5
JZRWXNBIQCMXSU-UHFFFAOYSA-N 2-(5-bromo-6-methoxynaphthalen-2-yl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=C(Br)C(OC)=CC=C21 JZRWXNBIQCMXSU-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
239000004305 biphenyl Substances 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
229910000396 dipotassium phosphate Inorganic materials 0.000 description 4
OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 4
238000005755 formation reaction Methods 0.000 description 4
239000002609 medium Substances 0.000 description 4
229960005137 succinic acid Drugs 0.000 description 4
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 3
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 3
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000002243 precursor Substances 0.000 description 3
229910052709 silver Inorganic materials 0.000 description 3
239000004332 silver Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
JZRWXNBIQCMXSU-QMMMGPOBSA-N (2s)-2-(5-bromo-6-methoxynaphthalen-2-yl)propanoic acid Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=C(Br)C(OC)=CC=C21 JZRWXNBIQCMXSU-QMMMGPOBSA-N 0.000 description 2
SCNNXOZSXWBSSI-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-methylbutan-1-one Chemical compound CC(C)CC(=O)C1=CC=C(Cl)C=C1 SCNNXOZSXWBSSI-UHFFFAOYSA-N 0.000 description 2
LWOTXBQKJLOAOZ-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)propan-1-one Chemical compound C1=C(OC)C=CC2=CC(C(=O)CC)=CC=C21 LWOTXBQKJLOAOZ-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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
101150047265 COR2 gene Proteins 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
229910052693 Europium Inorganic materials 0.000 description 2
QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 2
239000001358 L(+)-tartaric acid Substances 0.000 description 2
235000011002 L(+)-tartaric acid Nutrition 0.000 description 2
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 description 2
208000036366 Sensation of pressure Diseases 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000006286 aqueous extract Substances 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
125000005998 bromoethyl group Chemical group 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
229940093499 ethyl acetate Drugs 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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150000004694 iodide salts Chemical class 0.000 description 1
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150000002634 lipophilic molecules Chemical class 0.000 description 1
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235000010755 mineral Nutrition 0.000 description 1
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ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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238000006462 rearrangement reaction Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
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RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
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125000003107 substituted aryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
MDKGKXOCJGEUJW-UHFFFAOYSA-N suprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-UHFFFAOYSA-N 0.000 description 1
229960004492 suprofen Drugs 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000614747A 1984-04-06 1989-09-29 Procede pour la preparation d'acides ó-arylalcanoiques optiquement actifs, et nouveaux intermediaires de ceux-ci Expired - Fee Related CA1318917C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000614747A CA1318917C (fr)	1984-04-06	1989-09-29	Procede pour la preparation d'acides ó-arylalcanoiques optiquement actifs, et nouveaux intermediaires de ceux-ci

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
IT7207A/84		1984-08-06
IT07206/84A IT1199447B (it)	1984-08-06	1984-08-06	Intermedi utili per la sintesi di acidi carbossilici
IT8407207A IT1207420B (it)	1984-08-06	1984-08-06	Acidi carbossilici. procedimento per la preparazione di
IT7206A/84		1984-08-06
IT7204A/84		1984-08-06
CA000478585A CA1282410C (fr)	1984-04-06	1985-04-04	Methode de preparation d'acides ó-arylalcanoiques; nouveaux produits intermediaires
CA000614747A CA1318917C (fr)	1984-04-06	1989-09-29	Procede pour la preparation d'acides ó-arylalcanoiques optiquement actifs, et nouveaux intermediaires de ceux-ci

Publications (1)

Publication Number	Publication Date
CA1318917C true CA1318917C (fr)	1993-06-08

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Application Number	Title	Priority Date	Filing Date
CA000614747A Expired - Fee Related CA1318917C (fr)	1984-04-06	1989-09-29	Procede pour la preparation d'acides ó-arylalcanoiques optiquement actifs, et nouveaux intermediaires de ceux-ci

Country Status (1)

Country	Link
CA (1)	CA1318917C (fr)

1989
- 1989-09-29 CA CA000614747A patent/CA1318917C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2006-06-08	MKLA	Lapsed

Publication	Publication Date	Title
CA1282410C (fr)	1991-04-02	Methode de preparation d'acides ó-arylalcanoiques; nouveaux produits intermediaires
CA2184104C (fr)	2000-08-29	Preparation de 2-halo-1-(phenyle substitue)ethanol et d'oxyde de styrene substitue, optiquement actifs
CA1318917C (fr)	1993-06-08	Procede pour la preparation d'acides ó-arylalcanoiques optiquement actifs, et nouveaux intermediaires de ceux-ci
US5004832A (en)	1991-04-02	Preparing alpha-arylalkanoic acids
US4810819A (en)	1989-03-07	Process for the preparation of optically active alpha-acrylalkanoic acids and novel intermediates thereof
KR860001228B1 (ko)	1986-08-30	d-및 l-2-(6-메톡시-2-나프틸)-프로피온산 혼합물의 광학적 분할방법
JP2538540B2 (ja)	1996-09-25	光学活性カルボン酸及び関連中間体の製造方法
NO178335B (no)	1995-11-27	Optisk aktive r ved fremstilling av optisk aktive
DD234423A5 (de)	1986-04-02	Enantioselektives verfahren zur herstellung optischer aktiver - arylalkansaeure
Man	1988	Studies of Benzo-fused Tetranhenvlenes
JPH09124527A (ja)	1997-05-13	光学活性２−ハロ−１−（置換フェニル）エタノール類及び置換スチレンオキサイド類の製造方法及びその光学純度を高める方法
NO173055B (no)	1993-07-12	Fremgangsmaate for fremstilling av alfa-arylalkansyrer
JPS6025947A (ja)	1985-02-08	４−ヒドロキシ−２−シクロペンテノン類の製造法