Ind. -N-Alkylation of Tryptophan and Synthesis of 1-Alkyltryptophan Hydrazides

Abstract

A convenient method for the synthesis of 1-alkyltryptophans is described. The proof of ind. -N-alkylation was obtained from several data. Effect of 1-alkyl substitution of indole was observed on the ultraviolet spectra of 1-alkytryptophans. It was confirmed by debenzylation of L-1-benzyltryptophan in liquid ammonia that no racemization had occurred in the alkylation. 1-Alkyltryptophans were converted to hydrazides via methyl ester hydrochlorides in good yields.