Synthesis of D- and L-serine

Abstract

The optical resolution of DL-O-methylserinamide (V), the intermediate in the serine synthesis from acrylonitrile, was described. Resolution of DL-O-methylserinamide (V) was carried out with L-tartaric acid in methanol solution. The precipitated L-hydrogentartrate of L- V, m.p. 172∼173°(decomp.), [α]20D+12.57°(c=1, NHCl), was isolated from the methanol solution, and L-hydrogentartrate of D- V, m.p. 150∼151°(decomp.), [α]20D+0.29°(c=1, NHCl), was crystallized from the mother liquor. Hydrolysis of these optically active V with 47% HBr solution afforded the corresponding L-and D-serine (VI). The synthesized L-serine (VI) was found to correspond to natural serine.