METHOD FOR PRODUCING L-2-AMINO-4-(HYDROXYMETHYLPHOSPHINYL)- BUTANOIC ACID

Title:

METHOD FOR PRODUCING L-2-AMINO-4-(HYDROXYMETHYLPHOSPHINYL)- BUTANOIC ACID

Document Type and Number:

WIPO Patent Application WO/2006/104120

Kind Code:

A1

Abstract:

Disclosed is a method for efficiently and highly selectively producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid, which is useful as a herbicide, through a catalytic asymmetric synthesis reaction. Specifically disclosed is a method for producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid which is characterized in that a dehydroamino acid is subjected to an asymmetric hydrogenation by using a rhodium catalyst represented by the formula (2) below and having an optically active cyclic phosphine ligand, and then the resulting product is subjected to a hydrolysis. [Rh(R⁴)(L)]X (2) [In the formula, R⁴ represents 1,5-cyclooctadien or norbornadien; L represents a substance represented by the following formula (6): [Chemical formula 1] (6) (wherein R⁵ and R⁸ respectively represent a C_1-4 alkyl group; R⁶ and R⁷ respectively represent a hydrogen atom or a hydroxyl group; and Y represents a group selected from groups represented by the following formula (7): [Chemical formula 2] (7) (wherein Me represents a methyl group).]

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Inventors:

MINOWA NOBUTO (JP)
NAKANISHI NOZOMU (JP)
MITOMI MASAAKI (JP)

Application Number:

PCT/JP2006/306219

Publication Date:

October 05, 2006

Filing Date:

March 28, 2006

Export Citation:

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Assignee:

MEIJI SEIKA KAISHA (JP)
MINOWA NOBUTO (JP)
NAKANISHI NOZOMU (JP)
MITOMI MASAAKI (JP)

International Classes:

C07F9/30; C07B53/00

Domestic Patent References:

WO2003042135A2	2003-05-22
WO2003040149A2	2003-05-15

Foreign References:

JPS62226993A	1987-10-05
JP2002523419A	2002-07-30
JPS52139727A	1977-11-21
JPS5525A	1980-01-05
JPS59219297A	1984-12-10
JP2003528572A	2003-09-30
JP2003505031A	2003-02-12
JPS62132891A	1987-06-16
JPS62226993A	1987-10-05

Other References:

SINGH J. ET AL.: "Efficient Asymmetric Synthesis of the Vasopeptidase Inhibitor BMS-189921", ORGANIC LETTERS, vol. 5, no. 17, 2003, pages 3155 - 3158, XP003001233
See also references of EP 1864989A4
TETRAHEDRON LETT., 1987, pages 1255
TETRAHEDRON LETT., 1992, pages 8263
J. ORG. CHEM., vol. 56, 1991, pages 1783
CHEM. REV., vol. 103, 2003, pages 3029 - 3070
TETRAHEDRON, 1992, pages 8263
J. AM. CHEM. SOC., vol. 113, 1991, pages 8518
J. ORG. CHEM., vol. 63, 1998, pages 8031
J. ORG. CHEM., vol. 65, 2000, pages 3489
ANGEW. CHEM. INT. ED., vol. 39, 2000, pages 1981
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"J. Am. Chem. Soc.", vol. 99, 1977, pages: 5946
"JIKKEN KAGAKU KOZA", vol. 18, 1991, MARUZEN, pages: 339 - 344

Attorney, Agent or Firm:

Kato, Asamichi c/o A. Kato & Associates (daVinci BOSEI 7th Floor 20-12 Shin-Yokohama 3-chome, Kohoku-k, Yokohama-shi Kanagawa 33, JP)

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