Dimethylformamide → 6-(2-Aminoacetyl)amino-6-(2-chlorophenyl)-2-cyclohexen-1-one

Participants

Reaction Steps

A solution of 6-amino-6-(2-chlorophenyl)-2-cyclohexen-1-one (50 mg, 0.23 mmol), N-(tert-butoxycarbonyl)glycine (47 mg, 0.27 mmol), hydroxybenzotriazole (31 mg, 0.23 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (66 mg, 0.35 mmol) in dimethylformamide (1 ml) was stirred at room temperature for 18 h. The reaction was partitioned between saturated bicarbonate and ethyl acetate, the organic phase was washed with brine, dried (Na2SO4), and the solvent removed by evaporation. The residue was dissolved in dichloromethane (2 ml), trifluoroacetic acid (2 ml) was added and stirred at room temperature for 1 h, followed by evaporation of the solvent and a normal work up. Purification was achieved by preparative thin layer chromatography on silica gel eluting with ethyl acetate. Isolation of the UV and ninhydrin positive band at Rf 0.2 gave 6-(2-aminoacetyl)amino-6-(2-chlorophenyl)-2-cyclohexen-1-one (28 mg, 43%). The title compound was found to be active at 6μm in both the CMK and DAMI assay.

Provenance & Evidence