Title:
PROCESSES FOR PRODUCING GLUTAMIC ACID DERIVATIVE AND PYROGLUTAMIC ACID DERIVATIVE AND NOVEL INTERMEDIATE FOR PRODUCTION
Document Type and Number:
WIPO Patent Application WO/2004/067494
Kind Code:
A1
Abstract:
A process for producing a glutamic acid derivative represented by monatin, which comprises alkylating a 4-(protected hydroxy)pyroglutamic acid derivative with an alkylating agent to obtain a 4-(protected hydroxy)-4-alkylgultamic acid derivative and subjecting it to hydrolysis and protective-group elimination. The 4-(protected hydroxy)pyroglutamic acid derivative can be easily produced from hydroxyproline. The 4-(protected hydroxy)pyroglutamic acid derivative is selectively and stereoselectively alkylated in the 4-position and, after the alkylation, can be easily converted to a glutamic acid derivative. It can hence be advantageously used especially for efficiently producing monatin having a high optical purity.
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Inventors:
AMINO YUSUKE (JP)
Application Number:
PCT/JP2003/017016
Publication Date:
August 12, 2004
Filing Date:
December 26, 2003
Export Citation:
Assignee:
AJINOMOTO KK (JP)
AMINO YUSUKE (JP)
AMINO YUSUKE (JP)
International Classes:
C07C229/36; C07D207/28; A23L27/30; (IPC1-7): C07C227/22; C07C229/36; C07D207/28; C07D209/20; C07D403/06
Foreign References:
| US5128482A | 1992-07-07 | |||
| US5128164A | 1992-07-07 | |||
| ZA8704288A | ||||
| US5994559A | 1999-11-30 |
Other References:
NAKAMURA K. ET AL.: "Total synthesis of Monatin", ORGANIC LETTERS, vol. 2, no. 19, 2000, pages 2967 - 2970, XP002964364
GREENE T. W. ET AL., 1999, JOHN WILEY & SONS, INC., article "Protection groups in organic synthesis third edition", pages: 127 - 132, XP002968877
OLESEN P. ET AL.: "2(S),4(R)-4-(beta-D-galactopyranosyloxy)-4-isobutyl-glutsmic acid: A new amino acid in reseda odorata", PHYTOCHEMISTRY, vol. 12, 1973, pages 1713 - 1719, XP002976448
EZQUERRA J. ET AL.: "Stereoselective double alkylation of ethyl N-Boc-pyroglutamate", J. ORG. CHEM., vol. 59, 1994, pages 4327 - 4331, XP002976449
OLIVEIRA D.J. ET AL.: "Diastereoselective formation of a quaternary center in a pyroglutamate derivative. Formal synthesis of Monatin", TETRAHEDRON LETTERS, vol. 42, 2001, pages 6793 - 6796, XP004317777
C.W. HOLZAPFEL ET AL., SYNTHETIC COMMUNICATIONS, vol. 24, no. 22, 1994, pages 3197 - 3211
K. NAKAMURA ET AL., ORGANIC LETTERS, vol. 2, 2000, pages 2967 - 2970
D.J. OLIVEIRA ET AL., TETRAHEDRON LETTERS, vol. 42, 2001, pages 6793 - 6796
J. EZQUERRA ET AL., J. ORG. CHEM., vol. 59, 1994, pages 4327 - 4331
See also references of EP 1582514A4
GREENE T. W. ET AL., 1999, JOHN WILEY & SONS, INC., article "Protection groups in organic synthesis third edition", pages: 127 - 132, XP002968877
OLESEN P. ET AL.: "2(S),4(R)-4-(beta-D-galactopyranosyloxy)-4-isobutyl-glutsmic acid: A new amino acid in reseda odorata", PHYTOCHEMISTRY, vol. 12, 1973, pages 1713 - 1719, XP002976448
EZQUERRA J. ET AL.: "Stereoselective double alkylation of ethyl N-Boc-pyroglutamate", J. ORG. CHEM., vol. 59, 1994, pages 4327 - 4331, XP002976449
OLIVEIRA D.J. ET AL.: "Diastereoselective formation of a quaternary center in a pyroglutamate derivative. Formal synthesis of Monatin", TETRAHEDRON LETTERS, vol. 42, 2001, pages 6793 - 6796, XP004317777
C.W. HOLZAPFEL ET AL., SYNTHETIC COMMUNICATIONS, vol. 24, no. 22, 1994, pages 3197 - 3211
K. NAKAMURA ET AL., ORGANIC LETTERS, vol. 2, 2000, pages 2967 - 2970
D.J. OLIVEIRA ET AL., TETRAHEDRON LETTERS, vol. 42, 2001, pages 6793 - 6796
J. EZQUERRA ET AL., J. ORG. CHEM., vol. 59, 1994, pages 4327 - 4331
See also references of EP 1582514A4
Attorney, Agent or Firm:
Takahashi, Fumiko c/o AJINOMOTO CO. (INC. Intellectual Property Depa Property
Department, 1-1, Suzuki-cho, Kawasaki-k, Kawasaki-shi Kanagawa, JP)
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