Benzylamine → (R)-N-Benzyl-2-acetamido-3-hydroxypropionamide

Participants

Reaction Steps

N-Acetyl-D-serine methyl ester (25 g, 0.155 mole) was dissolved in benzylamine (33.2 g, 0.3101 mole) at 0-5° C. To this triethylamine (3.13 g, 0.031 mole) was added at 0-5° C. The reaction mixture was allowed to cool to room temperature and stirred for 12 hr. To the thick colorless precipitate formed 300 ml methyl tert-butyl ether was added and stirred for 6 hr. The product was filtered and dried under vacuum to obtain (R)-2-acetamido-N-benzyl-3-hydroxy-propionamide (34.03 g, Yield: 93%, HPLC: 98.9, Chiral HPLC: 98.8%)

Provenance & Evidence