Citric Acid → HCID 50990949, compound

Participants

Reaction Steps

270 mg (2.0 mmol) of 1-hydroxybenzotriazole and 390 mg (2.0 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride are added successively to a solution of 580 mg (1.7 mmol) of (S)-3-(4-but-2-ynyloxybenzoylamino)-2-piperidin-1-ylpropanoic acid in 15 ml of dimethylformamide. The reaction medium is stirred for 30 min at ambient temperature then 300 mg (2.0 mmol) of O-tert-butyldimethylsilylhydroxylamine in 5 ml of dimethylformamide are added. After stirring at ambient temperature for 18 h then hydrolysis with 2 ml of an aqueous solution of 5% citric acid, the reaction medium is stirred at ambient temperature for a further 30 min, then extracted with ethyl acetate. The ethyl acetate phase is washed with a saturated aqueous solution of sodium hydrogen carbonate then with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated. The residue obtained is purified by chromatography over silica gel eluted with a 98/2 dichloromethane/methanol mixture. 80 mg (13%) of 4-but-2-ynyloxy-N—((S)-2-hydroxycarbamoyl-2-piperidin-1-ylethyl)benzamide are obtained in the form of a white solid having a melting point of 144° C.

Provenance & Evidence