Aminoacetonitrile → HCID 86649022, compound

Participants

Reaction Steps

To a mixture of (1R,2R)-4-(2-Chloro-benzenesulfonyl)-2-(4-chloro-phenoxymethyl)-cyclopentanecarboxylic acid (epimeric mixture, 50 mg) in dimethylformamide (2 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (46 mg), hydroxybenzotriazole (24 mg) and ethyldiisopropylamine (61 mg). After 45 min, aminoacetonitrile (8 mg) was added and the reaction mixture was stirred for 2 days then partitioned between ethyl acetate and an aqueous saturated solution of sodium hydrogenocarbonate. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with dichloromethane/methanol (19:1 v/v) as eluant to afford the title compound (53 mg, 97%) as light yellow oil. MS (EI): 467.0 (M+H)+.

Provenance & Evidence