PRODUCTION OF ENANTIOMER-ENRICHED AMINO ACID, AMINO ACID DERIVATIVE AND AMINO ACID-ACID ADDITION SALT

摘要

PROBLEM TO BE SOLVED: To provide a method for ready and rapid production of the subject compounds useful as an intermediate for synthesis of a biologically active substance by reacting a nitron with a hydrazine derivative under a radical condition and subsequently hydrolyzing the resulting substance. ;SOLUTION: A diastereomer-enriched nitron of formula I (* is an asymmetric center; R1 is H, a 1-6C alkyl, a benzyl or the like) is reacted with a hydrazine derivative of formula II (R2 is H, a 1-6C alkyl, a 2-6C alkenyl or the like) preferably at -78 to +150°C in the presence of a radical initiator or under an electrochemical condition to form a diastereomer-enriched compound of formula III (R3 is OH). Subsequently the resulting compound is hydrolyzed or after the resulting compound is firstly reduced to a compound of formula III the reduced compound is hydrolyzed to give an enantiomer-enriched amino acid of formula IV (X is O or NH; R3 is H or OH), an amino acid derivative or an acid addition salt. This method readily and rapidly provides an objective amino acid from a readily available starting substance.;COPYRIGHT: (C)2000,JPO