4-Methylmorpholine → N-Hydroxy-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide

Participants

Reaction Conditions

Reaction Steps

Solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 451 mg, 2.35 mmol) is added to a solution of 3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic acid (595 mg, 1.96 mmol), 1-hydroxybenzotriazole hydrate (HOBT, 281 mg, 2.08 mmol) and 4-methylmorpholine (0.26 mL, 2.4 mmol) in CH2Cl2 (19 mL) and DMF (4 mL) at 0° C. The solution is stirred at 0° C. for 1 hour, and then a near solution of hydroxylamine hydrochloride (204 mg, 2.94 mmol) and 4-methylmorpholine (0.32 mL, 2.9 mmol) in DMF (2.7 mL) is added. After stirring at room temperature overnight, the mixture is concentrated under high vacuum, and purified by column chromatography (3% MeOH/CH2Cl2). Crystallization from Et2O/hexane provided 193 mg (31%) of the title compound as a white solid (mp 123°-124° C.).

Provenance & Evidence