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filingDate 1973-02-23-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1977-06-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber IE-37316-B1
titleOfInvention Processes for the production of optically active esters of alpha-amine acids
abstract 1423822 Optically active α-amino acid esters GLAXO LABORATORIES Ltd 20 Feb 1973 [25 Feb 1972 22 Dec 1972] 8902/72 and 59431/72 Heading C2C The invention provides a process for the production of an ester of one enantiomer of an α-amino acid in the form of a salt with an optically active acid which comprises reacting an acid of the opposite enantiomer of said α-amino acid (optionally in admixture with an ester of the desired enantiomer) with said optically active acid and an aldehyde or ketone, optionally in the form of an acetol, hemiacetal, ketal or hemiketal thereof, whereby an ester of the desired enantiomer separates out in the form of said salt. Preferred esters have Formula I in which R represents an optionally substituted C 1 -C 6 alkyl group, an optionally substituted C 5 -C 6 cycloalkyl group an aralkyl or aryl group and Ar represents an aryl group (including heteroaromatic groups) and the preferred acids are tartaric acid and dibenzyltartaric acid. The invention also provides esters of Formula II in which R is as defined above and R<SP>1</SP> is a substituted or unsubstituted acyl group other than unsubstituted phenyl, which are in substantially optically pure form, together with their (+) hemitartrate salts. N - Benzylidene ethyl DL - phenylglycinate is prepared by reaction of benzaldehyde with ethylphenylglycinate. Methyl and ethyl DL - p - hydroxyphenylglycinate are prepared by reacting DL-phydroxyphenylglycine with methanol and ethanol respectively in the presence of concentrated H 2 SO 4 . Other ring substituted phenyl glycinate esters are also prepared by refluxing the appropriately substituted phenylglycine with the appropriate alcohol in presence of concentrated H 2 SO 4 . N - Benzylidene methyl DL - p - hydroxyphenylglycinate is prepared by reacting methyl DL - p - hydroxyphenylglycinate with benzaldehyde. N - (p - Nitrobenzylidene)methyl DL - phydroxyphenylglycinate and N-(p-methoxybenzylidene)methyl DL - p - hydroxyphenylglycinate are prepared by reacting methyl DL-p-hydroxyphenyl glycinate with, respectively p-nitrobenzaldehyde and p-methyoxybenzaldehyde.n[GB1423822A]
priorityDate 1972-02-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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