N-Carboxyphenylhydrazido derivatives of glycine, DL-alanine, DL-phenylalanine, DL-leucine, and DL-tyrosine have been prepared by refluxing carboalkoxyamino acid phenylhydrazides with potassium hydroxide in ethanol. The 5-substituted 3-anilinohydantoins were isolated as intermediates in the above reactions. The N-carboxyphenylhydrazidoamino acids were oxidized with potassium permanganate to give N-phenylazocarbonyl derivatives of the amino acids. The N-carboxyphenylhydrazido-DL-amino acids were used as substrates in a papain-catalyzed reaction with phenylhydrazine to give N-carboxyphenylhydrazido-L-amino acid phenylhydrazides.added. This solution -was refluxed, for 4 hr., and then cooled, and the salt was separated by filtration and washed with hot methanol; the yield was 11.3 g. (65%), m.p. 212-214°.
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