Triethylamine → N-[1(S)-Benzyl-2-hydroxy-2-(4-methyl-3-oxopiperazin-2-yl)-ethyl]-acetamide hydrochloride

Participants

Reaction Steps

Stir overnight at room temperature under a nitrogen atmosphere a solution of acetic acid (25 μl, 0.45), 3-(2-(S)-amino-1-hydroxy-3-phenylpropyl)-1-methylpiperazin-2-one (120 mg, 0.45 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (112 mg, 0.58 mmol), triethylamine (0.12 mL, 0.9 mmol), dimethylaminopyridine (5.5 mg, 0.04 mmol) and 1-hydroxybenzotriazole hydrate (HOBt) (79 mg, 0.58 mmol) in dichloromethane (10 mL/mmol). Dilute with more dichloromethane and wash with, 5% aqueous sodium bicarbonate solution, saturated aqueous sodium chloride. Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 9:1 dichloromethane:methanol) to provide a white solid. Suspend the solid in 4 M HCl in 1,4-dioxane and stir for 10 min and concentrate the solution to give the title compound as a white solid (15 mg, 10%).

Provenance & Evidence