CS259510B2 - Method of optically active 2-(6-methoxy-2-naphtyl)propionic acid production - Google Patents
Method of optically active 2-(6-methoxy-2-naphtyl)propionic acid production Download PDFInfo
- Publication number
- CS259510B2 CS259510B2 CS829038A CS903882A CS259510B2 CS 259510 B2 CS259510 B2 CS 259510B2 CS 829038 A CS829038 A CS 829038A CS 903882 A CS903882 A CS 903882A CS 259510 B2 CS259510 B2 CS 259510B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- methoxy
- compound
- acid
- naphthyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 65
- 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 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title description 12
- 239000002253 acid Substances 0.000 claims abstract description 81
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 150000002148 esters Chemical group 0.000 claims abstract description 46
- 150000001408 amides Chemical group 0.000 claims abstract description 32
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 8
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 4
- -1 sulfonic acid anion Chemical class 0.000 claims description 88
- 230000008569 process Effects 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 28
- 239000011777 magnesium Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 150000004820 halides Chemical class 0.000 claims description 16
- 238000005907 ketalization reaction Methods 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 238000003797 solvolysis reaction Methods 0.000 claims description 9
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000002902 organometallic compounds Chemical class 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001449 anionic compounds Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- 150000002891 organic anions Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 27
- 150000002576 ketones Chemical class 0.000 abstract description 21
- 150000002905 orthoesters Chemical group 0.000 abstract description 17
- 238000007796 conventional method Methods 0.000 abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052793 cadmium Inorganic materials 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical group [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 abstract 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 47
- 239000000243 solution Substances 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 229910052799 carbon Inorganic materials 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- 230000003287 optical effect Effects 0.000 description 26
- 150000001721 carbon Chemical group 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 230000008707 rearrangement Effects 0.000 description 22
- 239000007818 Grignard reagent Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 14
- AYFJBMBVXWNYLT-UHFFFAOYSA-N 2-bromo-6-methoxynaphthalene Chemical compound C1=C(Br)C=CC2=CC(OC)=CC=C21 AYFJBMBVXWNYLT-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HIUDLIMYBWOTRX-JTQLQIEISA-N [(2s)-1-(6-methoxynaphthalen-2-yl)-1-oxopropan-2-yl] methanesulfonate Chemical compound C1=C(C(=O)[C@H](C)OS(C)(=O)=O)C=CC2=CC(OC)=CC=C21 HIUDLIMYBWOTRX-JTQLQIEISA-N 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- SQCGVOMRBGIXCW-ZDUSSCGKSA-N 2-[(2s)-2-chloro-1,1-diethoxypropyl]-6-methoxynaphthalene Chemical compound C1=C(OC)C=CC2=CC(C(OCC)([C@H](C)Cl)OCC)=CC=C21 SQCGVOMRBGIXCW-ZDUSSCGKSA-N 0.000 description 11
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 11
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
- 230000000707 stereoselective effect Effects 0.000 description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 150000004795 grignard reagents Chemical class 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 150000008065 acid anhydrides Chemical class 0.000 description 9
- 150000001266 acyl halides Chemical class 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
- MMYDBHAAEBBZCF-VKHMYHEASA-N [(2s)-1-chloro-1-oxopropan-2-yl] methanesulfonate Chemical compound ClC(=O)[C@H](C)OS(C)(=O)=O MMYDBHAAEBBZCF-VKHMYHEASA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000000010 aprotic solvent Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000001632 sodium acetate Substances 0.000 description 7
- 235000017281 sodium acetate Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- SBNAWXAVNWGSHY-VIFPVBQESA-N (2s)-2-chloro-1-(6-methoxynaphthalen-2-yl)propan-1-one Chemical compound C1=C(C(=O)[C@H](C)Cl)C=CC2=CC(OC)=CC=C21 SBNAWXAVNWGSHY-VIFPVBQESA-N 0.000 description 6
- LFMBKSRGQHUJKP-UHFFFAOYSA-N 2-methylsulfonyloxypropanoic acid Chemical compound OC(=O)C(C)OS(C)(=O)=O LFMBKSRGQHUJKP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 150000001502 aryl halides Chemical class 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 150000007517 lewis acids Chemical class 0.000 description 6
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 6
- 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 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- HIUDLIMYBWOTRX-SNVBAGLBSA-N [(2r)-1-(6-methoxynaphthalen-2-yl)-1-oxopropan-2-yl] methanesulfonate Chemical compound C1=C(C(=O)[C@@H](C)OS(C)(=O)=O)C=CC2=CC(OC)=CC=C21 HIUDLIMYBWOTRX-SNVBAGLBSA-N 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 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 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- LFMBKSRGQHUJKP-VKHMYHEASA-N (2s)-2-methylsulfonyloxypropanoic acid Chemical compound OC(=O)[C@H](C)OS(C)(=O)=O LFMBKSRGQHUJKP-VKHMYHEASA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical class CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- MMYDBHAAEBBZCF-GSVOUGTGSA-N [(2r)-1-chloro-1-oxopropan-2-yl] methanesulfonate Chemical compound ClC(=O)[C@@H](C)OS(C)(=O)=O MMYDBHAAEBBZCF-GSVOUGTGSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 235000014655 lactic acid Nutrition 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- MMYDBHAAEBBZCF-UHFFFAOYSA-N (1-chloro-1-oxopropan-2-yl) methanesulfonate Chemical compound ClC(=O)C(C)OS(C)(=O)=O MMYDBHAAEBBZCF-UHFFFAOYSA-N 0.000 description 3
- GIFLQCVVIWXBBS-NSHDSACASA-N (2s)-1,1-dimethoxy-1-(6-methoxynaphthalen-2-yl)propan-2-ol Chemical compound C1=C(C(OC)(OC)[C@H](C)O)C=CC2=CC(OC)=CC=C21 GIFLQCVVIWXBBS-NSHDSACASA-N 0.000 description 3
- XCOAABZEUNQHQG-VIFPVBQESA-N (2s)-2-bromo-1-(6-methoxynaphthalen-2-yl)propan-1-one Chemical compound C1=C(C(=O)[C@H](C)Br)C=CC2=CC(OC)=CC=C21 XCOAABZEUNQHQG-VIFPVBQESA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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- 239000003444 phase transfer catalyst Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229960000851 pirprofen Drugs 0.000 description 1
- PIDSZXPFGCURGN-UHFFFAOYSA-N pirprofen Chemical compound ClC1=CC(C(C(O)=O)C)=CC=C1N1CC=CC1 PIDSZXPFGCURGN-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical class CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- NGSFWBMYFKHRBD-UHFFFAOYSA-M sodium lactate Chemical compound [Na+].CC(O)C([O-])=O NGSFWBMYFKHRBD-UHFFFAOYSA-M 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229960004492 suprofen Drugs 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003475 thallium Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/313—Compounds having groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
-
- 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
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/02—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/02—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 2
- C07D317/06—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 2 condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
- Luminescent Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Seasonings (AREA)
- Transmission And Conversion Of Sensor Element Output (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32967281A | 1981-12-11 | 1981-12-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS903882A2 CS903882A2 (en) | 1988-03-15 |
| CS259510B2 true CS259510B2 (en) | 1988-10-14 |
Family
ID=23286496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS829038A CS259510B2 (en) | 1981-12-11 | 1982-12-10 | Method of optically active 2-(6-methoxy-2-naphtyl)propionic acid production |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP0081993B1 (da) |
| JP (4) | JPS58135833A (da) |
| KR (1) | KR890000375B1 (da) |
| AT (1) | ATE36517T1 (da) |
| AU (1) | AU560800B2 (da) |
| CA (2) | CA1259627A (da) |
| CS (1) | CS259510B2 (da) |
| DD (1) | DD206372A5 (da) |
| DE (1) | DE3278907D1 (da) |
| DK (6) | DK551782A (da) |
| ES (1) | ES518086A0 (da) |
| FI (2) | FI82680C (da) |
| GR (1) | GR77059B (da) |
| HK (1) | HK51489A (da) |
| HU (1) | HU191621B (da) |
| IE (1) | IE53922B1 (da) |
| IL (1) | IL67455A (da) |
| IN (1) | IN156354B (da) |
| IT (1) | IT1155421B (da) |
| MX (1) | MX159862A (da) |
| NO (1) | NO156650C (da) |
| NZ (1) | NZ202773A (da) |
| PH (5) | PH20529A (da) |
| PL (1) | PL142997B1 (da) |
| PT (1) | PT75973B (da) |
| RO (1) | RO87021B (da) |
| SG (1) | SG3089G (da) |
| SU (1) | SU1577694A3 (da) |
| ZA (1) | ZA829101B (da) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE53333B1 (en) * | 1980-09-11 | 1988-10-26 | Syntex Pharma Int | Process for preparing alpha-aromatic group substituted alkanoic acids or esters thereof |
| IT1208109B (it) * | 1983-11-23 | 1989-06-06 | Alfa Chem Ital | Procedimento per la risoluzione ottica di acidi arilpropionici |
| DE3461525D1 (en) * | 1984-02-02 | 1987-01-15 | Zambon Spa | Process for preparing alpha-arylalkanoic acids |
| IT1173216B (it) * | 1984-02-03 | 1987-06-18 | Zambon Spa | Processo per la preparazione di acidi alfa-idrossiaril-alcanoici |
| IT1174084B (it) * | 1984-05-10 | 1987-07-01 | Blaschim Spa | Procentimento per preparare il naproxen |
| US4670586A (en) * | 1984-09-12 | 1987-06-02 | Nippon Chemicals Co., Ltd. | Method for the production of α-aryl-alkanoic acid |
| IT1190362B (it) * | 1985-05-30 | 1988-02-16 | Zambon Spa | Preparazione del (6-metossi-2-naftil)-(1-bormoetil)-chetone e dei suoi derivati |
| IT1188181B (it) * | 1985-07-31 | 1988-01-07 | Zambon Spa | Processo per la preparazione di acidi carbossilici otticamente attivi e relativi intermedi |
| IT1198237B (it) * | 1986-12-23 | 1988-12-21 | Zambon Spa | Intermedi per la sintesi di composti organici |
| WO1989010350A1 (en) * | 1988-04-21 | 1989-11-02 | Ici Australia Operations Proprietary Limited | Preparation of an epoxide |
| EP0380316A3 (en) * | 1989-01-25 | 1990-11-28 | Syntex Pharmaceuticals International Limited | Preparation of alpha-methylareneacetic acids |
| IT1251958B (it) * | 1991-10-18 | 1995-05-27 | Zambon Spa | Processo per la dealogenazione di derivati del naftalene |
| JP3563406B2 (ja) * | 1994-06-08 | 2004-09-08 | 塩野義製薬株式会社 | ４−オキソ−２−アルケン酸エステルの製造方法 |
| JP3744060B2 (ja) * | 1996-06-20 | 2006-02-08 | ダイソー株式会社 | アシルオキシスルホン酸エステル誘導体の製造法 |
| US20050245764A1 (en) * | 2001-08-08 | 2005-11-03 | Koki Yamashita | Process for producing optically active 2-substituted carboxylic acid |
| PL368129A1 (en) | 2001-08-09 | 2005-03-21 | Ono Pharmaceutical Co, Ltd. | Carboxylic acid derivative compounds and drugs comprising these compounds as the active ingredient |
| SK16482002A3 (sk) * | 2002-11-20 | 2004-06-08 | Slovakofarma, A. S. | Spôsob prípravy substituovaných derivátov 2-aryl alkánových kyselín |
| CN106496092B (zh) * | 2016-08-30 | 2019-03-29 | 江苏宇田医药有限公司 | 一种用于合成西洛多辛的中间体的制备方法 |
| CN112110801B (zh) * | 2020-10-09 | 2022-07-19 | 浙江工业大学 | 一种γ-芳基取代酮类化合物的合成方法 |
| CN114644554A (zh) * | 2020-12-21 | 2022-06-21 | 上海医药工业研究院 | (s)-氟比洛芬的制备方法及其中间体 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637767A (en) * | 1968-07-30 | 1972-01-25 | Syntex Corp | 2-(6'-methoxynaphth-2'-yl)propylene oxide and 5'-halo derivatives |
| ES455064A1 (es) * | 1977-01-17 | 1978-02-01 | Valles Quimica | Nuevo procedimiento para la obtencion del acido (d)-2(6-me- toxi-2-naftil)-propionico. |
| JPS54115358A (en) * | 1978-02-25 | 1979-09-07 | Daito Koeki | Manufacture of 22*6**substituted naphthoo2**yl* propionic acid |
| JPS5519214A (en) * | 1978-07-27 | 1980-02-09 | Ono Pharmaceut Co Ltd | 2-acyl-6-aminomethylphenol derivative and its preparation |
| JPS55130934A (en) * | 1979-03-31 | 1980-10-11 | Masao Sato | Ketone synthesis from grignard reagent and acid halide |
| IT1212408B (it) * | 1980-02-26 | 1989-11-22 | Blaschim Spa | Processo per la produzione di acidi alcanoici alfa sostituiti. |
| IE50897B1 (en) * | 1980-02-26 | 1986-08-06 | Blaschim Spa | Process for preparing esters of alkanoic acids via rearrangement of alpha-haloketals |
| JPS5798232A (en) * | 1980-11-10 | 1982-06-18 | Sagami Chem Res Center | 1-(6-methoxy-2-naphthyl)-2-oxy-1-alkanone acetal |
| IE53333B1 (en) * | 1980-09-11 | 1988-10-26 | Syntex Pharma Int | Process for preparing alpha-aromatic group substituted alkanoic acids or esters thereof |
| IL65629A (en) * | 1981-04-30 | 1987-08-31 | Syntex Pharma Int | Preparation of alpha-arylalkanoic acids and esters and salts thereof |
| JPS5810525A (ja) * | 1981-06-15 | 1983-01-21 | Sagami Chem Res Center | 光学活性な１−芳香族基置換−１−アルカノン類の製造方法 |
-
1982
- 1982-12-07 FI FI824203A patent/FI82680C/fi not_active IP Right Cessation
- 1982-12-08 MX MX195510A patent/MX159862A/es unknown
- 1982-12-09 RO RO109274A patent/RO87021B/ro unknown
- 1982-12-09 PH PH28253A patent/PH20529A/en unknown
- 1982-12-10 ZA ZA829101A patent/ZA829101B/xx unknown
- 1982-12-10 EP EP82306603A patent/EP0081993B1/en not_active Expired
- 1982-12-10 JP JP57216765A patent/JPS58135833A/ja active Granted
- 1982-12-10 DE DE8282306603T patent/DE3278907D1/de not_active Expired
- 1982-12-10 CA CA000417445A patent/CA1259627A/en not_active Expired
- 1982-12-10 PT PT75973A patent/PT75973B/pt not_active IP Right Cessation
- 1982-12-10 AT AT82306603T patent/ATE36517T1/de not_active IP Right Cessation
- 1982-12-10 DD DD82245847A patent/DD206372A5/de not_active IP Right Cessation
- 1982-12-10 IT IT24665/82A patent/IT1155421B/it active
- 1982-12-10 GR GR70038A patent/GR77059B/el unknown
- 1982-12-10 CS CS829038A patent/CS259510B2/cs unknown
- 1982-12-10 PL PL1982239456A patent/PL142997B1/pl unknown
- 1982-12-10 IN IN1435/CAL/82A patent/IN156354B/en unknown
- 1982-12-10 SU SU823524059A patent/SU1577694A3/ru active
- 1982-12-10 ES ES518086A patent/ES518086A0/es active Granted
- 1982-12-10 NO NO824175A patent/NO156650C/no unknown
- 1982-12-10 IL IL67455A patent/IL67455A/xx not_active IP Right Cessation
- 1982-12-10 HU HU823988A patent/HU191621B/hu not_active IP Right Cessation
- 1982-12-10 IE IE2945/82A patent/IE53922B1/en not_active IP Right Cessation
- 1982-12-10 KR KR8205541A patent/KR890000375B1/ko active
- 1982-12-10 NZ NZ202773A patent/NZ202773A/en unknown
- 1982-12-10 AU AU91464/82A patent/AU560800B2/en not_active Ceased
- 1982-12-10 DK DK551782A patent/DK551782A/da not_active Application Discontinuation
-
1983
- 1983-03-27 PH PH30451A patent/PH21336A/en unknown
-
1984
- 1984-03-27 PH PH30452A patent/PH20059A/en unknown
- 1984-03-27 PH PH30453A patent/PH20169A/en unknown
-
1985
- 1985-07-18 PH PH32535A patent/PH22187A/en unknown
-
1988
- 1988-08-17 DK DK461388A patent/DK461388D0/da not_active Application Discontinuation
- 1988-08-17 DK DK461588A patent/DK461588A/da not_active Application Discontinuation
- 1988-08-17 DK DK461288A patent/DK461288A/da not_active Application Discontinuation
- 1988-08-17 DK DK461488A patent/DK461488A/da not_active Application Discontinuation
- 1988-08-17 DK DK461188A patent/DK461188A/da not_active Application Discontinuation
-
1989
- 1989-01-13 SG SG30/89A patent/SG3089G/en unknown
- 1989-06-29 HK HK514/89A patent/HK51489A/xx not_active IP Right Cessation
-
1990
- 1990-02-28 JP JP2049175A patent/JPH02262532A/ja active Pending
- 1990-02-28 JP JP2049173A patent/JPH02270840A/ja active Pending
- 1990-02-28 JP JP2049174A patent/JPH02262533A/ja active Granted
- 1990-03-26 FI FI901487A patent/FI901487A0/fi not_active Application Discontinuation
-
1992
- 1992-05-13 CA CA000616341A patent/CA1338433C/en not_active Expired - Fee Related
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