The Synthesis of D,L p-Vinylphenylglycine by Amidoalkylation, and its Reactions.

Article abstract of DOI:10.1016/S0040-4020(01)81353-3

Amidoalkylation of (2-chloroethyl)benzene or (2-bromoethyl)benzene with α-hydroxyhippuric acid and N-methoxycarbonyl α-hydroxyglycine, followed by dehydrohalogenation, affords N-protected p-vinylphenylglycines.Transformation of the vinyl group leads to N-methoxycarbonyl-p-<1-(methoxycarbonylamino)ethyl>phenylglycine, N-methoxycarbonyl-p-(epoxyethyl)phenylglycine, N-methoxycarbonyl-p-formylphenylglycine and N-methoxycarbonyl-p-carboxyphenylglycine.The deprotection of these compounds is described.