Question

Esters of aminoacids are commonly prepared and stored as hydrochloride salts; e.g., alanine methyl ester hydrochloride (below). One reason is that the electrostatically neutral forms of such esters (“free bases”) tend to turn into compounds called diketopiperazines upon standing. Write an accurate mechanism for the formation of the diketopiperazine derived from alanine methyl ester free base. Please show all steps.

1. Esters of aminoacids are commonly prepared and stored as hydrochloride salts; e.g., alanine methyl ester hydrochloride (below). One reason is that the electrostatically neutral forms of such esters ("free bases") tend to turn into compounds called diketopiperazines upon standing. Write an accurate mechanism for the formation of the diketopiperazine derived from alanine methyl ester free base. on standing, oN C) 03 it turns into: NH2 N O alanine methyl ester hydrochloride indefinitely stable alanine methyl ester free base a diketopiperazine

Answer 1

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