78981-25-6

15761-38-3

78981-25-6

GENERAL STEPS: To a stirred solution of N-tert-butoxycarbonyl-L-alanine (5.0 g, 26.4 mmol) in anhydrous tetrahydrofuran (THF) at -10 °C were sequentially added triethylamine (3 mL, 21.12 mmol) and ethyl chloroformate (2.5 mL, 26.4 mmol). The reaction mixture was stirred continuously at this temperature for 1 hour, followed by the passage of ammonia (NH3) for 1.5 hours. After completion of ammonia pass-through, the reaction mixture was transferred to room temperature conditions and continued stirring overnight. At the end of the reaction, the THF solvent was removed by distillation under reduced pressure. Subsequently, aqueous sodium chloride solution (40 mL) was added to the residue and extracted several times with ethyl acetate (EtOAc, 5 x 40 mL). The organic phases were combined, washed sequentially with 0.5 M hydrochloric acid (2 × 30 mL), dried with anhydrous sodium sulfate (Na2SO4), filtered, and the solvent was removed by vacuum evaporation to finally obtain the target product, N-Boc-D-alaninamide.