Process for preparing optically active 3-phenylglycidic acid esters

Patent 5244803 Issued on September 14, 1993. Estimated Expiration Date:

September 14, 2010. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Abstract Claims Description Full Text

Patent References

8-Chloro-1,5-benzothiazepine derivatives
Patent #: 4567175
Issued on: 01/28/1986
Inventor: Takeda , et al.

1,5-benzothiazepine derivatives and their pharmaceutical use
Patent #: 4590188
Issued on: 05/20/1986
Inventor: Takeda , et al.

Process for preparing optically active indoline-2-carboxylic acid
Patent #: 4898822
Issued on: 02/06/1990
Inventor: Asada, et al.

Resolution of glycidyl esters to high enantiomeric excess Patent #: 4923810
Issued on: 05/08/1990
Inventor: Walts, et al.

Inventors

Assignee

Tanabe Seiyaku Co., Ltd.

Application

No. 578904 filed on 09/07/1990

US Classes:

435/280, Resolution of optical isomers or purification of organic compounds or composition containing same435/123, Oxygen as only ring hetero atom435/824, Achromobacter435/832, Bacillus435/840, Brevibacterium435/843, Corynebacterium435/850, Flavobacterium435/859, Micrococcus435/863, Mycobacterium435/874, Pseudomonas435/878, Rhizobium435/910, Xanthomonas435/921, Candida435/938, Pichia540/491The chalcogen and the nitrogen are in the 1,5-positions of the bicyclo ring system (e.g., 1,5-benzothiazepinone, etc.)

Examiners

Primary: Robinson, Allen J.

Attorney, Agent or Firm

Browdy and neimark

Foreign Patent References

62433 AU. 03/13/1987
158339 EP. 04/13/1985
237983 EP. 03/13/1987
237080 EP 09/13/1987
0264457 EP. 04/13/1988
325954 EP. 08/13/1989
333142 EP 09/13/1989
343714 EP 11/13/1989
362556 EP 04/13/1990
90/643 WO 05/13/1990

International Class

C07D 281/02

Foreign Application Priority Data

1989-09-13 JP

Abstract

There is disclosed a process for preparing optically active 3-phenylglycidic acid ester compound, which comprises permitting a culture broth, cells or treated cells of a microorganism having an ability of stereoselectively hydrolyzing a (2R, 3S)-3-phenylglycidic acid ester compound to act on a racemic 3-phenylglycidic acid ester compound which may also have a substituent on the phenyl group, thereby hydrolyzing the (2R, 3S) optically active isomer and separating and collecting the (2S, 3R) antipode from the reaction mixture.

Other References

Tetrahedron, vol. 41, No. 7, (1985) pp. 1393-1399, Pergamon Press Ltd., GB; P. Melloni et al.: "Configurational studies on 2-[alpha-(2-ethoxyphenoxy)benzyl]morpholine FCE 20124" *Whole document*
Philippi, M. Chr. et al., "Enantioselective Hydrolysis and Transesterification of Glycidyl Butyrate by Lipase Preparations from Porcine Pancreas" ,: in Biocatalysis in Organic Media, C. Laane et al., (Ed.), Proceedings of an International Symposium held at Wageningen, The Netherlands, Dec. 7-10, 1986
Ladner, W. E., et al., "Lipase-Catalyzed Hydrolysis as a Route to Esters of Chiral Epoxy Alcohols," J. Am. Chem. Soc. 106:7250-7251 (1986)
Schneider, M. et al "Enzymatic Syntheses of Chiral Building Blocks from Racemates: Preparation of (1R,3R)-Chrysantemic-Permethrinic and --Casonic Acids from Racemic Diastereomeric Mixtures," Angew. Chem. Int. Ed. Engl. 23(1):64-66 (1984)
Schneider, M. et al., "Enzymatic Synthesis of Chiral Building Blocks from Prochiral Substrates: Enantioselective Synthesis of Monoalkyl Malonates," Angew. Chem., Int. Ed. Engl. 23(1):66 (1984)
Melloni, P. et al. "Configurational Studies of 2-[଱-(2-ethoxyphenoxy)Benzyl]Morpholine FCE 20123," Tetrahedron 41(7):1393-1399 (1985)
"Optically active 3-(p-methoxyphenyl)glcycidic acid derivatives," Chemical Abstracts 103:7119w, p. 638 (1985)
"Optically active potassium 3-(p-methoxyphenyl)=glycidate," Chemical Abstracts 103:71180q, p. 638 (1985