Resolution of racemic phenyl-glycinamide - by salt formation with (N)-acetyl-phenylglycine, inter. for penicillins and sweeteners (NL 25.4.77)

摘要

Prepn. of optically active phenylglycinamide (I) comprises converting a mixt. of L- and D- (I) completely or partially to its salt with optically active N-acetylphenylglycine (II). The appropriate (I) is then recovered from the ppte. which consists mainly of only one of the disastereoisomeric salts. Pref. salt formation is carried out in a solvent in which the diastereoisomeric salts have different solubilities. Salts of optically active (I) with L- or D- (II) are new. (I) is an intermediate for phenylglycine (III). D-(III) is an intermediate for alpha-aminobenzylpenicillin and L-(III) is an intermediate for the sweetener L-asparagine-L-phenylglycine alkyl ester. No expensive resolving agents are required since (II) is prepd. from (I) by hydrolysis then acetylation. When (I) is converted to (III) any residual (II) present is converted to the same prod.