4-Methylmorpholine → Boc-AlaAlaPro-OBzl

Participants

Reaction Steps

To a solution of 0.035 mole of t-butyloxycarbonylalanine in 80 ml of dry tetrahydrofuran which has been cooled to -20° to - 30° is added 4 ml of N-methylmorpholine and then 4.6 ml of isobutylchloroformate. After stirring for 10 minutes there is added 0.035 mole of alanylproline benzylester hydrochloride and 4 ml of N-methylmorpholine in 60 ml of chloroform. The reaction mixture is stirred overnight at room temperature, concentrated in vacuo and the residue taken up between ethyl acetate and 0.25 N hydrochloric acid. The organic layer is separated, washed with saturated sodium bicarbonate, water, dried over magnesium sulfate and concentrated in vacuo to give t-butoxycarbonylalanylalanylproline benzyl ester.

Provenance & Evidence