Patent ID: 6031121
Filing Date: 2000-02-29
Classification: C07C

Abstract:
A method of producing an optically active N-(2-acetylthiomethyl-1-oxo-3-phenylpropyl)-amino acid ester, represented by the general formula (IV): ##STR9## wherein R.sub.1 represents hydrogen, an amino acid side chain or a protected amino acid side chain; R.sub.2 represents a linear or branched C.sub.1 -C.sub.18 alkyl group, or a benzyl group which may or may not have a substituent; AcS represents an acetylthio group; and * represents an optically active carbon atom, the method comprisingreacting optically active 2-hydroxymethyl-3-phenylpropionic acid, represented by a general formula (I): ##STR10## wherein * represents the optically active carbon atom, with an amino acid ester or a salt thereof to form an optically active N-(2-hydroxymethyl-1-oxo-3-phenylpropyl)-amino acid ester, represented by a general formula (II): ##STR11## wherein R.sub.1 and R.sub.2 independently represent the same as described above; and * represents the optically active carbon atom,activating the hydroxyl group of the hydroxymethyl group at a 2-position for conversion into an optically active N-acylamino acid ester represented by a general formula (III): ##STR12## wherein R.sub.1 and R.sub.2 independently represent the same as described above; X represents chlorine, bromine, iodine, a linear, branched or cyclic C.sub.1 -C.sub.6 alkylsulfonyloxy group which may or may not have a substituent, or a C.sub.6 -C.sub.18 arylsulfonyloxy group; and * represents the optically active carbon atom, andfurther subjecting the optically active N-acylamino acid ester to reaction with a thioacetate salt or thioacetic acid in the presence of a base.