JPS61145174A - 新規な光学活性エポキシプロピオン酸エステル誘導体の製造法 - Google Patents
新規な光学活性エポキシプロピオン酸エステル誘導体の製造法Info
- Publication number
- JPS61145174A JPS61145174A JP26743484A JP26743484A JPS61145174A JP S61145174 A JPS61145174 A JP S61145174A JP 26743484 A JP26743484 A JP 26743484A JP 26743484 A JP26743484 A JP 26743484A JP S61145174 A JPS61145174 A JP S61145174A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy
- methoxyphenyl
- acid ester
- optically active
- preparation
- Prior art date
- 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.)
- Granted
Links
- -1 epoxypropionic acid ester Chemical class 0.000 title description 4
- 239000002253 acid Substances 0.000 claims abstract description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract 2
- 150000007530 organic bases Chemical class 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- CUHUYVNPCQYRLG-UHFFFAOYSA-N 3-(4-methoxyphenyl)oxirane-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1C(C(O)=O)O1 CUHUYVNPCQYRLG-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 8
- FEDJGPQLLNQAIY-UHFFFAOYSA-N 2-[(6-oxo-1h-pyridazin-3-yl)oxy]acetic acid Chemical compound OC(=O)COC=1C=CC(=O)NN=1 FEDJGPQLLNQAIY-UHFFFAOYSA-N 0.000 abstract description 6
- 229960005316 diltiazem hydrochloride Drugs 0.000 abstract description 6
- 239000007858 starting material Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- WALQGLYYNPGHTK-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]1=CC=CC=C1Cl WALQGLYYNPGHTK-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 102100028138 F-box/WD repeat-containing protein 7 Human genes 0.000 description 2
- 101001060231 Homo sapiens F-box/WD repeat-containing protein 7 Proteins 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical class OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Epoxy Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26743484A JPS61145174A (ja) | 1984-12-20 | 1984-12-20 | 新規な光学活性エポキシプロピオン酸エステル誘導体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26743484A JPS61145174A (ja) | 1984-12-20 | 1984-12-20 | 新規な光学活性エポキシプロピオン酸エステル誘導体の製造法 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10199893A Division JPH06298751A (ja) | 1993-04-05 | 1993-04-05 | 塩酸ジルチアゼムの製造法 |
| JP10199793A Division JPH06287183A (ja) | 1993-04-05 | 1993-04-05 | 新規な光学活性エポキシプロピオン酸エステル誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61145174A true JPS61145174A (ja) | 1986-07-02 |
| JPH0428268B2 JPH0428268B2 (OSRAM) | 1992-05-13 |
Family
ID=17444788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26743484A Granted JPS61145174A (ja) | 1984-12-20 | 1984-12-20 | 新規な光学活性エポキシプロピオン酸エステル誘導体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61145174A (OSRAM) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008411A (en) * | 1988-05-24 | 1991-04-16 | Hoffmann-La Roche Inc. | Glycidic acid ester and process of preparation |
| US5013835A (en) * | 1989-01-11 | 1991-05-07 | Synthelabo | Method of preparing (+)-(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)2,3-dihydro-5H-1,5-benzothiazepine-4-one |
| AU616517B2 (en) * | 1988-05-18 | 1991-10-31 | Aventis Pharmaceuticals Inc. | Improved resolution of 3-(4-methoxyphenyl)glycidic acid with in situ conversion to alkyl esters |
| US5081277A (en) * | 1988-10-03 | 1992-01-14 | Synthelabo | Process for the preparation of propionic acid derivatives |
| US5256803A (en) * | 1990-02-21 | 1993-10-26 | Rhone-Poulenc Rorer S.A. | Process for the preparation of (2R,3R)-cis)-β-phenylglycidic acid |
| USRE34935E (en) * | 1989-01-11 | 1995-05-09 | Synthelabo | Method for preparing (+)-(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-5H-1,5-benzothiazepine-4-one and chlorinated derivatives thereof |
| US5998637A (en) * | 1997-02-27 | 1999-12-07 | Tanabe Seiyaku Co., Ltd. | Process for preparing optically active trans-3-substituted glycidic acid ester |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59196881A (ja) * | 1983-04-21 | 1984-11-08 | Shionogi & Co Ltd | 新規なエポキシド誘導体 |
| JPS6013776A (ja) * | 1983-07-05 | 1985-01-24 | Sawai Seiyaku Kk | 光学活性３−（ｐ−アルコキシフエニル）グリシツド酸誘導体の製造法 |
-
1984
- 1984-12-20 JP JP26743484A patent/JPS61145174A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59196881A (ja) * | 1983-04-21 | 1984-11-08 | Shionogi & Co Ltd | 新規なエポキシド誘導体 |
| JPS6013776A (ja) * | 1983-07-05 | 1985-01-24 | Sawai Seiyaku Kk | 光学活性３−（ｐ−アルコキシフエニル）グリシツド酸誘導体の製造法 |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU616517B2 (en) * | 1988-05-18 | 1991-10-31 | Aventis Pharmaceuticals Inc. | Improved resolution of 3-(4-methoxyphenyl)glycidic acid with in situ conversion to alkyl esters |
| US5008411A (en) * | 1988-05-24 | 1991-04-16 | Hoffmann-La Roche Inc. | Glycidic acid ester and process of preparation |
| US5081277A (en) * | 1988-10-03 | 1992-01-14 | Synthelabo | Process for the preparation of propionic acid derivatives |
| US5013835A (en) * | 1989-01-11 | 1991-05-07 | Synthelabo | Method of preparing (+)-(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)2,3-dihydro-5H-1,5-benzothiazepine-4-one |
| US5102998A (en) * | 1989-01-11 | 1992-04-07 | Synthelabo | Method for preparing (+)-(2s,3s)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-5h-1,5-benzothiazepine-4-one and chlorinated derivatives thereof |
| USRE34935E (en) * | 1989-01-11 | 1995-05-09 | Synthelabo | Method for preparing (+)-(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-5H-1,5-benzothiazepine-4-one and chlorinated derivatives thereof |
| US5256803A (en) * | 1990-02-21 | 1993-10-26 | Rhone-Poulenc Rorer S.A. | Process for the preparation of (2R,3R)-cis)-β-phenylglycidic acid |
| US5998637A (en) * | 1997-02-27 | 1999-12-07 | Tanabe Seiyaku Co., Ltd. | Process for preparing optically active trans-3-substituted glycidic acid ester |
| US6197953B1 (en) | 1997-02-27 | 2001-03-06 | Tanabe Seiyaku Co., Ltd. | Process for preparing optically active trans-3-substituted glycidic acid ester |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0428268B2 (OSRAM) | 1992-05-13 |
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