PROCESS FOR PRODUCING OPTICALLY ACTIVE CARBOXYLIC ACID SUBSTITUTED IN 2-POSITION

Title:

PROCESS FOR PRODUCING OPTICALLY ACTIVE CARBOXYLIC ACID SUBSTITUTED IN 2-POSITION

Document Type and Number:

WIPO Patent Application WO/2001/055074

Kind Code:

A1

Abstract:

A nitrous acid salt is added at a temperature of 10 to 80°C to an aqueous solution which contains an optically active 2-aminocarboxylic acid (4) and a protonic acid, the amount of the latter acid being 1 to 3 equivalents to the former, and which has a proton concentration of 0.5 to 2 mol/kg to conduct a reaction to thereby produce an optically active 2-hydroxycarboxylic acid (1). Thionyl chloride and a basic compound are caused to act on the compound (1) to chlorinate it and simultaneously invert the configuration in the 2-position. Thus, an optically active 2-chlorocarboxylic acid chloride (5) is induced. The compound (5) is hydrolyzed to induce an optically active 2-chlorocarboxylic acid (2). The compound (2) is reacted with a thioacetic acid salt to incorporate an acetylthio group thereinto and simultaneously invert the configuration in the 2-position to thereby produce an optically active 2-acetylthiocarboxylic acid (3).

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Inventors:

AMANO SUSUMU (JP)
MITSUDA MASARU (JP)
INOUE KENJI (JP)
KINOSHITA KOICHI (JP)
YAMASHITA KOKI (JP)
UEDA YASUYOSHI (JP)

Application Number:

PCT/JP2001/000470

Publication Date:

August 02, 2001

Filing Date:

January 25, 2001

Export Citation:

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Assignee:

KANEKA CORP (JP)
AMANO SUSUMU (JP)
MITSUDA MASARU (JP)
INOUE KENJI (JP)
KINOSHITA KOICHI (JP)
YAMASHITA KOKI (JP)
UEDA YASUYOSHI (JP)

International Classes:

C07C51/04; C07C51/367; C07C51/60; C07C59/48; C07C327/32; (IPC1-7): C07C51/367; C07C51/43; C07C59/48; C07C51/60; C07C51/04; C07C327/32

Foreign References:

JPS6479134A	1989-03-24
JPS4924914A	1974-03-05
JPS6479133A	1989-03-24
JPH10310567A	1998-11-24
US4371699A	1983-02-01
JPH107614A	1998-01-13
EP0159254A1	1985-10-23
JPH09295963A	1997-11-18
EP0110225A1	1984-06-13

Other References: