Pyridine → t-Butoxycarbonyltryptophan fluoride

Participants

Reaction Conditions

Reaction Steps

To a cooled (-15° C.) solution of t-butoxycarbonyltryptophan (1.2 g, 4 mmol) and pyridine (0.35 ml, 4 mmol) in methylene chloride (10 ml) is dropped cyanuric fluoride (0.72 ml, 36 mmol) and the mixture is stirred at -15° C. for 1 hour. The reaction mixture is diluted with methylene chloride and ice, and filtered on Celite. The filtrate is diluted with ice water and extracted with methylene chloride. The organic layer is dried over magnesium sulfate and concentrated in vacuo to give t-butoxycarbonyltryptophan fluoride.

Provenance & Evidence