1-Hydroxybenzotriazole → HCID 49854306, compound

Participants

Reaction Steps

150 mg (1.1 mmol) of 1-hydroxybenzotriazole and 210 mg (1.1 mmol) of 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride are added to a solution of 420 mg (1.0 mmol) of (S)-3-(4-benzyloxybenzenesulfonylamino)-2-piperidin-1-ylpropanoic acid in 15 ml of dimethylformamide. The reaction medium is stirred for 20 min and then a solution of 160 mg (1.1 mmol) of O-tert-butyldimethylsilylhydroxylamine in 3 ml of dimethylformamide is added. The reaction medium is then stirred at ambient temperature for 18 h and then hydrolyzed with 2 ml of a saturated aqueous solution of sodium hydrogen carbonate and 2 ml of water. After stirring for 20 min in order to complete the deprotection of the hydroxamate, the product is extracted with ethyl acetate. The organic phases are washed with a saturated aqueous solution of sodium hydrogen carbonate and then with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue obtained is crystallized from isopropyl ether under hot conditions, and then filtered off. The resulting solid is recrystallized from a 1/1 heptane/ethyl acetate mixture, filtered and then oven-dried under vacuum for 4 h. 150 mg of (S)-3-(4-benzyloxybenzenesulfonylamino)-N-hydroxy-2-piperidin-1-ylpropionamide are obtained in the form of a beige solid with a melting point of 126° C.

Provenance & Evidence