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Title:
PROCESS FOR PRODUCING OPTICALLY ACTIVE &agr -METHYLCYSTEINE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2005/007865
Kind Code:
A1
Abstract:
Optically active &agr -methylcysteine derivative is efficiently produced from an inexpensive raw material. An optically active 2-amino-2-methyl-1,3-propanediol derivative monoester is produced by esterifying one of the hydroxyls of 2-amino-2-methyl-1,3-propanediol derivative, which can be prepared from an extremely inexpensive raw material, under the action of a hydrolase in a highly stereoselective manner, or by hydrolyzing one of the esters of a diester of 2-amino-2-methyl-1,3-propanediol derivative under the action of a hydrolase in a stereoselective manner. Further, the optically active 2-amino-2-methyl-1,3-propanediol derivative monoester is subjected to hydroxyl sulfonation, ester hydrolysis, oxidation and reaction with a sulfurizing agent, thereby obtaining an optically active &agr -methylcysteine derivative.

Inventors:
UEDA MAKOTO (JP)
NANBA HIROKAZU (JP)
OHISHI TAKAHIRO (JP)
SUGAWARA MASANOBU (JP)
MORI KOUHEI (JP)
IZUMIDA MASASHI (JP)
Application Number:
PCT/JP2004/009245
Publication Date:
January 27, 2005
Filing Date:
June 23, 2004
Export Citation:
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Assignee:
KANEKA CORP (JP)
UEDA MAKOTO (JP)
NANBA HIROKAZU (JP)
OHISHI TAKAHIRO (JP)
SUGAWARA MASANOBU (JP)
MORI KOUHEI (JP)
IZUMIDA MASASHI (JP)
International Classes:
C07C219/04; C07C303/26; C07C319/08; C12P7/62; C12P13/12; (IPC1-7): C12P13/12; C07C271/16; C07C309/16; C07C319/02; C07C323/59
Foreign References:
JP2002167382A2002-06-11
JP2002316985A2002-10-31
JPH0319698A1991-01-28
JPH01503196A1989-11-02
JPS61158961A1986-07-18
Other References:
WANG Y-F, ET AL: "Lipase-catalyzed irreversible transesterifications using enol esters as acylating reagents: preparative enantio- and regioselective syntheses of alcohols, glycerol derivatives, sugars, and organometallics", J. AM. CHEM. SOC., vol. 110, no. 21, 1988, pages 7200 - 7205, XP001083909
AKAI S, ET AL: "Lipase-catalyzed asymmetric desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl benzoate", CHEM. PHARM. BULL., vol. 48, no. 10, 2000, pages 1519 - 1523, XP002981784
WANG Y-F, ET AL: "Lipase-catalyzed irreversible transesterification for preparative synthesis of chiral glycerol derivatives", J. ORG. CHEM., vol. 53, no. 13, 1988, pages 3127 - 3129, XP002981785
HATAKEYAMA S, ET AL: "Et2A1c1-catalyzed cyclization of epoxytrichloroacetimidates for the synthesis of alpha-substituted serines", J. ORG. CHEM., vol. 62, no. 7, 1997, pages 2275 - 2279, XP002197950
HATAKEYAMA S, ET AL: "Total synthesis of (+)-conagenin", TETRAHEDRON LETTERS, vol. 37, no. 23, 1996, pages 4047 - 4050, XP002945491
Attorney, Agent or Firm:
KANEKA CORPORATION (kita-ku Osaka-sh, Osaka 88, JP)
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