Water → HCID 53681965, compound

Participants

Reaction Steps

In methylene chloride was dissolved 200 mg of 1-(p-aminobenzyl)-5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1H-imidazole (104a), there were added 116 mg of dimethylaminopyridine and 212 μl of acetic anhydride under ice-cooling, and the mixture was allowed to warm up to room temperature and stirred for 1 hour. After completion of the reaction, the mixture was diluted with water, extracted with methylene chloride, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (methylene chloride:ethyl acetate=2:1)to provide 2-acetoxymethyl-1-(p-N-acetylaminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole. The compound was dissolved in 10 ml of methanol, and under ice-cooling, 1 ml of 1M sodium methoxide solution was added. The mixture was allowed to warm up to room temperature and stirred for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, and 41.2 mg of Compound I-117 was obtained (yield 19%).

Provenance & Evidence