Potassium Iodide → HCID 70053829, compound

Participants

Reaction Steps

N-Benzyloxycarbonyl-L-phenylalanyl-L-alanine bromomethyl ketone (50 mg, 0.11 mmol) and 2,6-dimethylphenol (14 mg) were dissolved in dry DMF (5 mL) and blanketed with argon gas. The solution was treated with potassium iodide on alumina (80 mg, KF-alumina, 2:3) and stirred overnight at room temperature. Ethyl acetate was added and the inorganic salts were removed by filtration. The organic filtrate was washed with saturated NaCl solution (4×25 mL), then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was applied to a silica gel column. Then N-benzyloxycarbonyl-L-phenylalanyl-L-alanine 2,6-dimethylphenoxymethyl ketone was eluted with EtOAc/hexane (1:1) under pressure. Evaporation gave a white solid (30 mg, 49%), m.p. 167°-168° C.

Provenance & Evidence