Tert-butoxycarbonylalanine → BOC-D-alanine

Participants

Reaction Steps

0.6 g of (R)-fenchol, 0.14 g of DMAP and 1.0 g of BOC-Ala-OH were dissolved in 30 mL of dichloromethane at 0° C. 2.0 g of EDIC were added and the reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was extracted with dichloromethane versus water. The organic layer was washed with 1N HCl, NaHCO3 and brine, dried over MgSO4 and concentrated. The crude product was purified using column chromatography, to give 0.3 g of colorless oil (24%).

Provenance & Evidence