Z-PHG-OH

2935-35-5

501-53-1

5491-18-9

General procedure for the synthesis of the compound (CAS:5491-18-9) from L-phenylglycine and benzyl chloroformate: To an aqueous solution (500 mL) containing 2-amino-2-phenylacetic acid (20 g, 0.12 mol), sodium carbonate (27.97 g, 0.264 mol) and sodium bicarbonate (11.1 g, 0.132 mol) were added at room temperature. The mixture was stirred until a clarified solution was formed. Acetone (40 mL) was then added and the resulting slightly turbid solution was cooled to 15-20 °C in an ice water bath. Benzyl chloroformate (Cbz-Cl, 28.15 g, 0.165 mol) was added slowly with stirring and then the reaction mixture was gradually warmed to room temperature. After continued stirring for 3 h, the reaction mixture was extracted with methyl tert-butyl ether (100 mL). The pH of the aqueous layer was adjusted with aqueous hydrochloric acid to 2. The oil formed was extracted with ethyl acetate (100 mL x 2). The organic layers were combined, washed with water and concentrated under vacuum to give (S)-2-(((benzyloxy)carbonyl)amino)-2-phenylacetic acid (30.2 g, 80% yield) as a white solid.