Triethylamine → N-[2-tert-butoxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]-4-but-2-ynyloxybenzamide

Participants

Reaction Steps

50 mg (0.4 mmol) of 1-hydroxybenzotriazole then 70 mg (0.4 mmol) of 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide hydrochloride are added to a solution of 100 mg (0.2 mmol) of 3-(4-but-2-ynyloxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoic acid in 2 ml of dichloromethane and 2 ml of dimethylformamide. The reaction medium is stirred for 20 min before adding a mixture containing 30 mg (0.3 mmol) of O-tert-butylhydroxylamine hydrochloride and 40 μl (0.3 mmol) of triethylamine. The mixture is then stirred at ambient temperature for 20 h. Dichloromethane is added, the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate then with water, dried over magnesium sulphate, filtered and concentrated under vacuum. 100 mg (85%) of N-[2-tert-butoxycarbamoyl-2-(4-methanesulphonylpiperazin-1-yl)ethyl]-4-but-2-ynyloxy benzamide are obtained in the form of a white solid.

Provenance & Evidence