Methanol → HCID 86652856, compound

Participants

Reaction Steps

2-(2-{7-(2-{[Di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl)acetamide (262 mg) was dissolved in tetrahydrofuran (2 mL), tetrabutylammonium fluoride (0.5 mL) was added, and the mixture was stirred at room temperature for 15 hr. Saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (methanol:ethyl acetate=0:100 to 10:90, volume ratio) to give the title compound (144 mg, yield 81%) as a white solid. The obtained white solid was recrystallized from ethyl acetate-hexane to give colorless crystals. melting point 137-142° C. MS 504 (MH+).

Provenance & Evidence