Studies on the Synthensis of Amino Acids by the Schmidt Reaction. V.¹⁾ Synthensis of Phenylalanine Anaglogs.

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It has previously been reported that aliphatic amino acid was obtained from alkylmalonic acid using the Schmidt reaction, in a good yield. In this report the synthesis of more than twenty kinds of phenylalanine analogs from arylmalonic acid is described and furthermore, the effect of the benzene ring and its substituents on the reaction was examined, and some new information were obtained. 1) When the group of malonic acid combines directly with the benzene ring, the yield was considerably good. 2) In the case of benzylmalonic acids, when the electronegative group exists in the benzene ring, the expected amino acid was obtained, though in a low yield, but in the case with the positive group in the benzene ring, the expected amino acid was scarcely obtained. 3) From benzylmalonic acid the yield of amino acid was 18%, but from cyclohexyl-ethylmalonic acid, the yield of cyclohexylalanine was 50%.