Chemistry of Amino Acids. V. Studies on α-Alkyl-α-amino Acids. IX. Mild Hydrolytic Ring Cleavage of Hydantoin Derivatives

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It was found that hydantoin nuclei (Ia-d) were easily hydrolysed with caustic alkali to give hydantoic acid derivatives (IIIa-c) by way of 3-tosylhydantoin derivatives (IIa-d). IIIa-c were further hydrolyzed to amino acids with diluted hydrochloric acid. The hydrolysis of IId with alkali did not furnish the hydantoic acid derivative IIId but gave N-tolylsulfonyl-2-amino-2-isobutyl-4-methylvaleramide VI, probably due to the steric effect.