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)
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:
Assignee:
KANEKA CORP (JP)
UEDA MAKOTO (JP)
NANBA HIROKAZU (JP)
OHISHI TAKAHIRO (JP)
SUGAWARA MASANOBU (JP)
MORI KOUHEI (JP)
IZUMIDA MASASHI (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:
JP2002167382A | 2002-06-11 | |||
JP2002316985A | 2002-10-31 | |||
JPH0319698A | 1991-01-28 | |||
JPH01503196A | 1989-11-02 | |||
JPS61158961A | 1986-07-18 |
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
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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