Derivatives of 6-aminopenicillanic acid. Part XI. α-Amino-p-hydroxy-benzylpenicillin

Abstract

α-Amino-p-hydroxyphenylacetic acid was resolved and the isomeric amino-acids were coupled with 6-aminopenicillanic acid by two methods to give both epimers of α-amino-p-hydroxybenzylpenicillin. The epimer derived from (–)-D-α-amino-p-hydroxyphenylacetic acid has a broad spectrum of antibacterial activity and is exceptionally well absorbed into the bloodstream after administration by mouth.