THE SYNTHESIS OF D,L-α-AMINO-ε-HYDROXYCAPROIC ACID AND A NEW SYNTHESIS OF D,L-LYSINE

Abstract

δ-Hydroxyvaleraldehyde, obtained by acid hydrolysis of dihydropyran, is a convenient starting material for the synthesis of D,L-lysine. Application to the aldehyde of the Bucherer modification of the Strecker synthesis for α-amino acids yields 5-δ-hydroxybutylhydantoin which is hydrolyzed into D,L-α-amino-ε-hydroxycaproic acid. D,L-Lysine is obtained from 5-δ-hydroxybutylhydantoin by bromination with hydrobromic acid into 5-δ-bromobutylhydantoin, amination of the bromo compound with ammonia, and hydrolysis of the hydantoin ring into D,L-lysine, readily isolated as the dipicrate.