PROCESSES FOR PRODUCING $g(b)-HALOGENO-$g(a)-AMINO-CARBOXYLIC ACIDS AND PHENYLCYSTEINE DERIVATIVES AND INTERMEDIATES THEREOF

Title:

PROCESSES FOR PRODUCING $g(b)-HALOGENO-$g(a)-AMINO-CARBOXYLIC ACIDS AND PHENYLCYSTEINE DERIVATIVES AND INTERMEDIATES THEREOF

Document Type and Number:

WIPO Patent Application WO/1999/033785

Kind Code:

A1

Abstract:

An industrially advantageous process for producing $g(b)-halogeno-$g(a)-aminocarboxylic acids; and a process for producing optically active N-protected-S-phenylcysteine having a high optical purity and its intermediates with the use of the former process. The process for producing $g(b)-halogeno-$g(a)-aminocarboxylic acids or salts thereof comprises treating with a halogenating agent a $g(b)-hydroxy-$g(a)-aminocarboxylic acid (wherein the basicity of the amino group at the $g(a)-position is not shielded by the presence of the substituent of the amino group) or a salt thereof with an acid to thereby halogenate the hydroxyl group. The process for producing optically active N-protected-S-phenylcysteine represented by general formula (3) or its salt comprises subjecting optically active serine or its salt to the above-mentioned production process and then treating the product with an amino-protective agent followed by a reaction with thiophenol under basic conditions.

Inventors:

YAMASHITA KOKI (JP)
INOUE KENJI (JP)
KINOSHITA KOICHI (JP)
UEDA YASUYOSHI (JP)
MURAO HIROSHI (JP)

Application Number:

PCT/JP1998/005983

Publication Date:

July 08, 1999

Filing Date:

December 28, 1998

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Assignee:

KANEKA CORP (JP)
YAMASHITA KOKI (JP)
INOUE KENJI (JP)
KINOSHITA KOICHI (JP)
UEDA YASUYOSHI (JP)
MURAO HIROSHI (JP)

International Classes:

C07C227/16; C07C319/14; C07C229/20; C07C323/58; C07C323/59; (IPC1-7): C07C229/20; C07C227/16; C07C227/40; C07C323/58; C07C319/14; C07B53/00

Foreign References:

JPS60152499A	1985-08-10
JPS51149208A	1976-12-22
JPS60258161A	1985-12-20

Other References:

SHIRAIWA T., ET AL.: "OPTICAL RESOLUTION BY PREFERENTIAL CRYSTALLIZATION OF (2RS,3SR)-2-AMINO-3-CHOROBUTANOIC ACID HYDROCHLORIDE.", CHIRALITY., WILEY-LISS, NEW YORK., US, vol. 09., no. 07., 1 January 1997 (1997-01-01), US, pages 656 - 660., XP002920150, ISSN: 0899-0042, DOI: 10.1002/(SICI)1520-636X(1997)9:7<656::AID-CHIR3>3.0.CO;2-5

Attorney, Agent or Firm:

Yasutomi, Yasuo (4F 14-22, Nishinakajima 5-chome Yodogawa-ku Osaka-shi Osaka, JP)

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