Ethanol → HCID 71677820, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid (50 mg, 0.13 mmol) in ethanol (3 mL) was added conc. sulfuric acid (0.1 mL) and the reaction mixture was stirred at 95° C. for 14 h. The reaction mixture was then concentrated under vacuum, diluted with water, extracted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and purified by column chromatography (using 5% EtOAc in hexane as eluent) to give (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid ethyl ester (28 mg, 52.3% yield) as a blue sticky liquid. MS calcd. for C25H33N2O4 [(M+H)+] 425.0, obsd. 425.2.

Provenance & Evidence