PRODUCTION OF OPTICALLY ACTIVE 4-MERCAPTO-2-PYRROLIDONE DERIVATIVE AND ITS SYNTHETIC INTERMEDIATE

Japanese Patent JP2701685

B2

PURPOSE: To obtain the subject derivative useful as a synthetic intermediate for a carbapenem-based antimicrobial agent, etc., efficiently and in a high yield by subjecting a specific optically active aminomercaptobutyric acid (salt), etc., to ring closure reaction, eliminating a protective group.
CONSTITUTION: Racemic 4-amino-3-mercaptobutyric acid (salt) is reacted with optically active 1-(2,3,4-trichlorophenyl)ethanesulfonic acid (salt), difference in solubility of formed two kinds of diastereomer salts is used and optically active 4-amino-3-mercaptobutyric acid 1-(2,3,4-trichlorophenyl)ethaneslfonate, one slightly soluble diastereomer salt is separated and decomposed. Optically active 4-amino-3-mercaptobutyric acid obtained by the decomposition, its salt, the compound containing the protected amino group and/or mercapto group or a reactive derivative at the carboxyl group of these compounds is subjected to ring closure reaction to produce a compound of formula I [R11S is (protected) mercapto; NR21 is (protected) imino], which is deprotected to give the objective derivative of formula II.

Iwa Saki Tameo
Kazuhiko Kondo
Tadashi Nakatani
Yoshioka Ryuzo

JP34897092A

January 21, 1998

December 28, 1992

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Tanabe Pharmaceutical Co., Ltd.

C07B53/00; C07B57/00; C07C309/24; C07C319/28; C07C323/58; C07D207/273; C07D477/02; C07D207/26; (IPC1-7): C07D207/273; C07B53/00; C07C309/24; C07C323/58

JP59170057A
JP4103584A
JP5271169A
JP4724007B1

Shigeo Minoura

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