The Chlorinolysis of Methionine Derivatives

Abstract

The chlorinolysis of L-methionine methyl ester hydrochloride with molecular chlorine was carried out under various conditions, resulting in methyl L-2-amino-4, 4, 4-trichlorobutanoate and methyl L-2-amino-3, 4, 4, 4-tetrachlorobutanoate which were isolated as N-benzoyl and N-carbobenzoxy derivatives. The chlorinolysis of N-acylmethionine ester and methionine sulfoxide ester proceeded also without cleavage of the N-protecting group to give the same products as above. However, the reaction of methionine sulfone derivative with chlorine did not proceed in the same conditions.
It was proved that the resulting polychloroamino acid derivatives are optically pure.
The possible chlorinolysis mechanism was also proposed.