JPS57188563A - Preparation of optically active 3-benzoylthio-2-methyl- propionic acid - Google Patents
Preparation of optically active 3-benzoylthio-2-methyl- propionic acidInfo
- Publication number
- JPS57188563A JPS57188563A JP7377881A JP7377881A JPS57188563A JP S57188563 A JPS57188563 A JP S57188563A JP 7377881 A JP7377881 A JP 7377881A JP 7377881 A JP7377881 A JP 7377881A JP S57188563 A JPS57188563 A JP S57188563A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- salts
- alanineamide
- hypotensor
- benzoylthio
- 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.)
- Pending
Links
- BCAYPPFBOJCRPN-UHFFFAOYSA-N 3-benzoylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(=O)C1=CC=CC=C1 BCAYPPFBOJCRPN-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- OBSIQMZKFXFYLV-QMMMGPOBSA-N L-phenylalanine amide Chemical compound NC(=O)[C@@H](N)CC1=CC=CC=C1 OBSIQMZKFXFYLV-QMMMGPOBSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- BWKMGYQJPOAASG-VIFPVBQESA-N (3s)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CN[C@H](C(=O)O)CC2=C1 BWKMGYQJPOAASG-VIFPVBQESA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To prepare the titled compound useful as an intermediate of a hypotensor, by reacting the racemic titled compound with an optically active phenyl- alanineamide as a resolving agent, and separating the produced two kinds of optically active salts taking advantage of their solubility difference.
CONSTITUTION: Racemic 3-benzolthio-2-methylpropionic acid and an optically active phenyl-alanineamide are dissolved and mixed in a proper solvent (preferably ethyl acetate) to produce the corresponding salts. Either (2S) or (2R) optically active salt is precipitated as a crystal taking advantage of the solubility difference of the two kinds of salts, and the salt is decomposed to obtain the corresponding free carboxylic acid.
EFFECT: The troublesome process for the separation of isomers becomes unnescessary in the synthesis of a hypotensor by the condensation reaction with (3S)-1,2, 3,4-tetrahydroisoquinoline-3-carboxylic acid.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7377881A JPS57188563A (en) | 1981-05-15 | 1981-05-15 | Preparation of optically active 3-benzoylthio-2-methyl- propionic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7377881A JPS57188563A (en) | 1981-05-15 | 1981-05-15 | Preparation of optically active 3-benzoylthio-2-methyl- propionic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS57188563A true JPS57188563A (en) | 1982-11-19 |
Family
ID=13527994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7377881A Pending JPS57188563A (en) | 1981-05-15 | 1981-05-15 | Preparation of optically active 3-benzoylthio-2-methyl- propionic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57188563A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3424440A1 (en) * | 1983-07-04 | 1985-01-17 | Mitsubishi Rayon Co., Ltd., Tokio/Tokyo | METHOD FOR PRODUCING OPTICALLY ACTIVE CARBONIC ACIDS AND THEIR ESTERS IN THE FORM OF THE OPTICAL ANTIPODES |
| JPS6012992A (en) * | 1983-07-04 | 1985-01-23 | Mitsubishi Rayon Co Ltd | Production of optically active carboxylic acid |
| JPS6094091A (en) * | 1983-10-27 | 1985-05-27 | Mitsubishi Rayon Co Ltd | Production of optically active carboxylic acid ester |
| CN102864203A (en) * | 2012-03-20 | 2013-01-09 | 常州制药厂有限公司 | Preparation method for anti-hypertension medicine intermediate |
-
1981
- 1981-05-15 JP JP7377881A patent/JPS57188563A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3424440A1 (en) * | 1983-07-04 | 1985-01-17 | Mitsubishi Rayon Co., Ltd., Tokio/Tokyo | METHOD FOR PRODUCING OPTICALLY ACTIVE CARBONIC ACIDS AND THEIR ESTERS IN THE FORM OF THE OPTICAL ANTIPODES |
| JPS6012992A (en) * | 1983-07-04 | 1985-01-23 | Mitsubishi Rayon Co Ltd | Production of optically active carboxylic acid |
| JPS6094091A (en) * | 1983-10-27 | 1985-05-27 | Mitsubishi Rayon Co Ltd | Production of optically active carboxylic acid ester |
| CN102864203A (en) * | 2012-03-20 | 2013-01-09 | 常州制药厂有限公司 | Preparation method for anti-hypertension medicine intermediate |
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