Pyridine → HCID 9965205, compound

Participants

Reaction Steps

To a solution of (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid (1.0 g, 3.77 mmol) in dichloromethane (18 mL) at −35° C. was added dry pyridine (320 μL, 3.96 mmol) and cyanuric fluoride (477 μL, 5.65 mmol) under an atmosphere nitrogen. The mixture was stirred for 1.5 hours while maintaining the temperature between −35 and −25° C. Ice was added to the reaction mixture and the mixture was stirred for 15 minutes. The organic layer was separated and the aqueous layer extracted with dichloromethane (2×10 mL). The combined organic extracts were washed with ice cold water (15 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give ((S)-1-fluorocarbonyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester which was used in the subsequent step without further purification.

Provenance & Evidence