Methanol → Methyl 2-{5-[(3,5-dimethylphenyl)sulfanyl]-1,2-dimethyl-1H-imidazol-4-yl}propanoate

Participants

Reaction Steps

In 5 ml of methanol/diethyl ether (1/3 v/v %) saturated with hydrogen chloride was dissolved 60 mg (0.21 mmol) of 2-[1,2-dimethyl-5-(3,5-dimethylphenylthio)-1H-imidazol-4-yl]propiononitrile (43a), and the mixture was left at 4° C. for 23 hours. To the reaction mixture, 2 ml of methanol and 0.3 ml of water were added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution and extracted with methylene chloride. The organic layer was washed with water and dried over sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate) to obtain 57 mg of Compound I-96 as oil (yield 85%).

Provenance & Evidence