2,3-Dihydroxybutanedioic Acid → (R)-Amino-phenyl-acetic acid ethyl ester

Participants

Reaction Steps

A solution of ethyl DL-phenylglycinate (5.051 g., contains 0.05 mole methylene chloride i.e. 27.5 mmole) and (+)-tartaric acid (4.264 g., 28.4 mmole, 1.03 equiv.) in methanol: acetone (1:1, 50 ml.) was stirred at 20° to 25°; crystallisation began immediately. After 231/2 hours the mixture was filtered and the product washed with solvent (2 × 12 ml.) and dried at 24°/2 mm. for 31/2 hours giving ethyl D-phenylglycinate (+)-hemitartrate solvated with 1.0 mole methanol (7.265g., 73%), [α]D24 - 47.4° (c 2.519, H2O).

Provenance & Evidence