Imidazole → HCID 178483628, compound

Participants

Reaction Steps

To an ice-cooled solution of 200 mg (0.46 mmol) trans-methanesulfonic acid 3-(4-{2-[(4-chloro-phenoxycarbonyl)-methyl-amino]-ethyl}-cyclohexyl)-propyl ester (example 11.16) and 126 mg (1.85 mmol) of imidazole in 3.5 ml of N,N-dimethylformamide was added at 0° C. 30.3 mg (0.69 mmol) of sodium hydride (55% in oil). The reaction mixture was then stirred for 4 hours at room temperature. After quenching with ammonium chloride solution, the reaction mixture was partitioned between water and ether. The combined ether phases were washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 95:5 v/v mixture of ethylacetate and methanol as the eluent giving 103 mg (55%) of pure trans-{2-[4-(3-imidazol-1-yl-propyl)-cyclohexyl]-ethyl}-methyl-carbamic acid 4-chloro-phenyl ester as colorless viscous oil, MS: 404 (MH+).

Provenance & Evidence