The Optical Activation of N-Benzoylphenylglycine via the Salt of Optically Active 1-Phenylethylamine

Abstract

The optical activation of N-benzoylphenylglycine (RS[1]) was realized when its salt of (R)-1-phenylethylamine (R[2]) was refluxed in 100 times its weight of toluene followed by gradual concentration of the solution to a half its original volume. The product which contained 71.7% of S[1]-R[2] was obtained in a 77% yield. The degrees of asymmetric transformation from R[1]-R[2] to S[1]-R[2] were measured under various conditions. The attempt to obtain optically pure S[1] from RS[1]-R[2] was made successfully by modifing above procedure. R[1] also was obtained in the same way when RS[1]-S[2] was used instead of RS[1]-R[2].