Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1998-12-03
1999-11-09
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
562443, 562445, 562449, C07C20506, C07C22928
Patent
active
059817941
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for producing an optically active homophenylalanine derivative of the general formula (IV): ##STR2## (wherein X.sup.1 and X.sup.2 are the same or different and each represents a hydrogen atom, an alkyl group 1 to 7 carbon atoms, an aryl group containing 6 to 10 carbon atoms, an aralkyl group containing 7 to 10 carbon atoms, a hydroxyl group, a halogen atom, a cyano group, a trifluoromethyl group, an alkoxyl group containing 1 to 4 carbon atoms, an alkylmercapto group containing 1 to 4 carbon atoms or a nitro group), to an intermediate therefor, namely a .gamma.-oxo-homophenylalanine derivative, and to a process for the production thereof.
The optically active homophenylalanine derivative which is represented by the above general formula (IV) (hereinafter referred to as "homophenylalanine derivative (IV)") is an amino acid that is very important as a constituent of medicinals, in particular an angiotensin converting enzyme inhibitor (hereinafter referred to as "ACE inhibitor").
As is described in Japanese Kokai Publication Sho-64-71934, the above-mentioned homophenylalanine derivative (IV) can be readily derived into said ACE inhibitor following conversion of its amino group to a hydroxy group by reaction with nitrous acid.
BACKGROUND ART
Among the so-far known processes for producing the above-mentioned optically active homophenylalanine derivative (IV), there is a process using a biocatalyst such as an enzyme, and the process employing the so-called asymmetric synthesis without using any biocatalyst such as an enzyme.
As the above-mentioned process using a biocatalyst, Japanese Kokai Publication Hei-01-79134, for instance, discloses a process involving asymmetric decomposition of a corresponding hydantoin with hydantoinase, and Japanese Kokai Publication Hei-02-31694 discloses a process comprising asymmetrically hydrolyzing a corresponding aminonitrile with nitrile hydrolase. These processes, however, require the use of a toxic hydrocyanic acid compound in raw material synthesis.
U.S. Pat. No. 5,316,943 discloses a process comprising trans-amination of a corresponding keto acid with transaminase and, in the Journal of Organic Chemistry, vol. 55, page 5567 (1990), there is disclosed a process comprising reductively aminating a corresponding keto acid using phenylalanine dehydrogenase. These processes, however, require the use of an expensive keto acid as a material.
In the Journal of the American Chemical Society, vol. 112, page 945 (1990), there is disclosed a process which comprises asymmetrically hydrolyzing a corresponding ester using an enzyme and, in the Bulletin of the Chemical Society of Japan, vol. 55, page 918 (1982), there is disclosed a process comprising asymmetrically hydrolyzing a corresponding acetyl derivative using acylase. These processes, however, are processes for racemic resolution, hence, theoretically, the desired compounds can be obtained only in half amounts relative to the total amounts of starting racemates. Another disadvantage lies, for example, in the complexity of operational procedure.
As the above-mentioned process comprising asymmetric synthesis, there may be mentioned the process in which a chloroacetyl containing compound is reduced with an asymmetric boron complex followed by rearrangement (the Journal of the American Chemical Society, vol. 114, page 1906 (1992)), the process comprising hydrogenating a 4-phenyl-2-aminocrotonic acid derivative with an asymmetric rhodium complex (the Journal of Organic Chemistry, vol. 52, page 5142 (1987)) and the process comprising reacting an optically active glycine derivative with phenylpropyl bromide (the Journal of the American Chemical Society, vol. 108, page 1103 (1986)), among others. These processes for asymmetric synthesis, however, require the use of an expensive catalyst or an organometallic compound difficult to handle.
As the above-mentioned process comprising optical resolution of the optically active homophenylalanine derivative (IV), there may be mentioned,
REFERENCES:
patent: 4686084 (1987-08-01), Geke et al.
Database CAPLUS on STN, Acc. No. 1997:749970, Griesbeck et al., `A simple approach to beta amino acids by acylation of arenes with N-acylaspartic anhydrides.` Synlett (1997), (11), pp. 1243-1244. abstract, 1997.
Hasegawa Junzo
Nagashima Nobuo
Yamada Masahiko
Davis Brian J.
Geist Gary
Kaneka Corporation
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