Ammonium Hydroxide → HCID 178490884, compound

Participants

Reaction Steps

A mixture of 5-carboxy-3-(3-chloro-4-methoxybenzyl)-1-(trans-4-hydroxycyclohexyl)-2,3-dihydro-1H-benzimidazol-2-one (72 mg), ammonium hydroxide (0.1 mL, 28% NH3 in water), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (35.2 mg) and 1-hydroxybenzotriazole (27.1 mg) in anhydrous dimethylformamide (1 mL) was stirred at ambient temperature for 4 hours. The mixture was partitioned between water and ethyl acetate. The separated organic layer was washed successively with an aqueous saturated sodium bicarbonate solution, water, 1N-hydrochloric acid and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a preparative silica gel column chromatography eluting with 5% methanol in chloroform. The obtained solid was washed with acetonitrile to give 5-carbamoyl-3-(3-chloro-4-methoxybenzyl)-1-(trans-4-hydroxycyclohexyl)-2,3-dihydro-1H-benzimidazol-2-one (217.9 mg) as a colorless solid.

Provenance & Evidence