Title:
PROCESS FOR PRODUCING OPTICALLY ACTIVE CYSTEINE DERIVATIVES
Document Type and Number:
WIPO Patent Application WO/1999/036399
Kind Code:
A1
Abstract:
A process whereby optically active cysteine derivatives having a high optical purity and excellent qualities can be economically advantageously produced at a high efficiently even on an industrial scale. This process comprises reacting an optically active amino acid derivative in the D- or L-form represented by general formula (1): (wherein R?1¿ represents an amino-protective group of the urethane or acyl type; R?0¿ represents hydrogen or R?0¿ and R?1¿ together form an amino-protective group; R?2¿ represents alkyl, aryl or aralkyl; and * represents the location of an asymmetric carbon atom) with an alcohol represented by general formula (3): R?3¿-OH (wherein R?3¿ represents a monovalent organic group), a strong acid and/or a thionyl halide to thereby synthesize an optically active cysteine derivative in the D- or L-form represented by general formula (2), and then recovering the cysteine derivative from the liquid reaction mixture, wherein the successive procedures from the reaction to the recovery are effected under such conditions that n a medium being in contact with the cysteine derivative is an acidic to weakly basic one, thereby recovering the optically active cysteine derivative from the liquid reaction mixture while inhibiting the degradation and racemization of the derivative.
Inventors:
UEDA YASUYOSHI (JP)
MURAO HIROSHI (JP)
KONDO TAKESHI (JP)
UEYAMA NOBORU (JP)
MANABE HAJIME (JP)
YONEDA KENJI (JP)
NISHIYAMA AKIRA (JP)
MURAO HIROSHI (JP)
KONDO TAKESHI (JP)
UEYAMA NOBORU (JP)
MANABE HAJIME (JP)
YONEDA KENJI (JP)
NISHIYAMA AKIRA (JP)
Application Number:
PCT/JP1999/000074
Publication Date:
July 22, 1999
Filing Date:
January 13, 1999
Export Citation:
Assignee:
KANEKA CORP (JP)
UEDA YASUYOSHI (JP)
MURAO HIROSHI (JP)
KONDO TAKESHI (JP)
UEYAMA NOBORU (JP)
MANABE HAJIME (JP)
YONEDA KENJI (JP)
NISHIYAMA AKIRA (JP)
UEDA YASUYOSHI (JP)
MURAO HIROSHI (JP)
KONDO TAKESHI (JP)
UEYAMA NOBORU (JP)
MANABE HAJIME (JP)
YONEDA KENJI (JP)
NISHIYAMA AKIRA (JP)
International Classes:
C07C319/20; C07C319/28; C07C323/59; (IPC1-7): C07C323/59; C07C319/20; C07C319/28; C07B53/00; C07B57/00
Foreign References:
| JPH0751077A | 1995-02-28 |
Other References:
LANKIEWICZ L, ET AL.: "RESOLUTION OF RACEMIC AMINO ACIDS WITH THERMITASE", BIOORGANIC CHEMISTRY., ACADEMIC PRESS INC., NEW YORK, NY., US, vol. 17, 1 January 1989 (1989-01-01), US, pages 275 - 280, XP002930784, ISSN: 0045-2068, DOI: 10.1016/0045-2068(89)90029-1
USAPAY G., ET AL.: "SYNTHESIS, CRYSTAL STRUCTURE AND CONFORMATION IN SOLUTION OF FOUR STEREOISOMERIC CYCLO-LANTHIONINE DERIVATIVES.", INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH., MUNKSGAARD, COPENHAGEN., DK, vol. 46., 1 January 1995 (1995-01-01), DK, pages 290 - 301., XP002922801, ISSN: 0367-8377
See also references of EP 1054000A4
USAPAY G., ET AL.: "SYNTHESIS, CRYSTAL STRUCTURE AND CONFORMATION IN SOLUTION OF FOUR STEREOISOMERIC CYCLO-LANTHIONINE DERIVATIVES.", INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH., MUNKSGAARD, COPENHAGEN., DK, vol. 46., 1 January 1995 (1995-01-01), DK, pages 290 - 301., XP002922801, ISSN: 0367-8377
See also references of EP 1054000A4
Attorney, Agent or Firm:
Yasutomi, Yasuo (4F 14-22, Nishinakajima 5-chome Yodogawa-ku Osaka-shi Osaka, JP)
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