Title:
PROCESS FOR PRODUCING OPTICALLY ACTIVE β-HYDROXY-&agr -AMINOCARBOXYLIC ACID DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2006/075651
Kind Code:
A1
Abstract:
[PROBLEMS] To provide a process for efficiently producing the anti isomer of an optically active β-hydroxy-&agr -aminocarboxylic acid derivative useful as an intermediate for medicines/agricultural chemicals. [MEANS FOR SOLVING PROBLEMS] The process, which is for producing an optically active β-hydroxy-&agr -aminocarboxylic acid derivative represented by the formula (2) or (3) [Chemical formula 3] (wherein R1 means (un)substituted C1-20 alkyl or an (un)substituted C4-12 aromatic group and R2 means (un)substituted C1-20 alkyl or an (un)substituted C4-12 aromatic group), comprises hydrogenating an &agr -aminoacylacetic ester compound represented by the formula (1): [Chemical formula 1] [wherein R1 and R2 have the same meanings as defined above] in the presence of an acid through a catalytic asymmetric hydrogenation reaction employing as a catalyst a rhodium complex having as a ligand an optically active compound represented by the formula (4), (4'), or (5): [Chemical formula 2] the process being characterized in that the hydrogenation is conducted in the presence of an acetic acid salt.
Inventors:
HAMADA YASUMASA (JP)
MAKINO KAZUISHI (JP)
MAKINO KAZUISHI (JP)
Application Number:
PCT/JP2006/300275
Publication Date:
July 20, 2006
Filing Date:
January 12, 2006
Export Citation:
Assignee:
NISSAN CHEMICAL IND LTD (JP)
HAMADA YASUMASA (JP)
MAKINO KAZUISHI (JP)
HAMADA YASUMASA (JP)
MAKINO KAZUISHI (JP)
International Classes:
C07C227/16; B01J31/24; C07B53/00; C07C229/36; C07C269/04; C07C271/22; C07D307/54; C07D317/60; C07D333/16; C07B61/00
Domestic Patent References:
| WO2005005371A1 | 2005-01-20 |
Foreign References:
| JPH07118282A | 1995-05-09 | |||
| JPH0680617A | 1994-03-22 | |||
| JPH02172956A | 1990-07-04 | |||
| EP0612758A1 | 1994-08-31 |
Other References:
LABEEUW O. ET AL.: "Total synthesis of sulfobacin A through dynamic kinetic resolution of a racemic beta-keto-alpha-amino ester hydrochloride", TETRAHEDRON: ASYMMETRY, vol. 15, no. 12, 2004, pages 1899 - 1908, XP004519012
GENET J.P. ET AL. 002944740: "ASYMMETRIC SYNTHESIS. PRACTICAL PRODUCTION OF D AND L THREONINE. DYNAMIC KINETIC RESOLUTION IN RHODIUM AND RUTHENIUM CATALYZED HYDROGENATION OF 2-ACYLAMINO-3-OXOBUTYRATES", TETRAHEDRON: ASYMMETRY, vol. 2, no. 7, 1991, pages 555 - 567, XP002944740
KUWANO R. ET AL.: "Catalytic Asymmetric Synthesis of beta-Hydroxy-alpha-amino Acids: Highly Enantioselective Hydrogenation of beta-Oxy-alpha-acetamidoacrylates", JOURNAL OF ORGANIC CHEMISTRY, vol. 63, no. 10, 1998, pages 3499 - 3503, XP003000252
J. AM. CHEM. SOC., vol. 111, 1989, pages 9134 - 9135
SYNTHESIS, 1992, pages 1248 - 1254
"Asymmetric Catalysis in Organic Synthesis", 1994, JHON WILEY &; SONS, INC
TETRAHEDRON: ASYMMETRY, vol. 2, no. 7, 1991, pages 555 - 567
GENET J.P. ET AL. 002944740: "ASYMMETRIC SYNTHESIS. PRACTICAL PRODUCTION OF D AND L THREONINE. DYNAMIC KINETIC RESOLUTION IN RHODIUM AND RUTHENIUM CATALYZED HYDROGENATION OF 2-ACYLAMINO-3-OXOBUTYRATES", TETRAHEDRON: ASYMMETRY, vol. 2, no. 7, 1991, pages 555 - 567, XP002944740
KUWANO R. ET AL.: "Catalytic Asymmetric Synthesis of beta-Hydroxy-alpha-amino Acids: Highly Enantioselective Hydrogenation of beta-Oxy-alpha-acetamidoacrylates", JOURNAL OF ORGANIC CHEMISTRY, vol. 63, no. 10, 1998, pages 3499 - 3503, XP003000252
J. AM. CHEM. SOC., vol. 111, 1989, pages 9134 - 9135
SYNTHESIS, 1992, pages 1248 - 1254
"Asymmetric Catalysis in Organic Synthesis", 1994, JHON WILEY &; SONS, INC
TETRAHEDRON: ASYMMETRY, vol. 2, no. 7, 1991, pages 555 - 567
Attorney, Agent or Firm:
Hanabusa, Tsuneo c/o Hanabusa, Patent Office (Shin-Ochanomizu Urban Trinity 2,
Kandasurugadai 3-chom, Chiyoda-ku Tokyo 62, JP)
Download PDF:
Previous Patent: ENDOSCOPE-USE INSERTION UNIT
Next Patent: SEMICONDUCTOR DEVICE FOR DRIVING LED, AND LED DRIVING DEVICE
Next Patent: SEMICONDUCTOR DEVICE FOR DRIVING LED, AND LED DRIVING DEVICE