Hydrochloric Acid → HCID 57443475, compound

Participants

Reaction Conditions

Reaction Steps

2 N Hydrochloric acid aqueous solution (0.2 mL) was added to a solution of t-butyl-(1-{2-[4-(1-ethyl-1-{4-[5-(2-methoxy-vinyl)-furan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)-dimethyl-silane (Example 4-(1); 20 mg, 0.033 mmol) in tetrahydrofuran (0.5 mL) at room temperature, and the mixture was stirred at 65° C. for two hours. Tetrahydrofuran (0.3 mL) and 4 N hydrochloric acid aqueous solution (0.2 mL) were further added to the mixture at room temperature, and the mixture was stirred at 65° C. for two hours. A saturated aqueous sodium bicarbonate solution and ethyl acetate were added to the reaction mixture. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=3/1). The resulting product (6 mg) was dissolved in water (0.1 mL) and t-butanol (0.4 mL). Sodium dihydrogenphosphate (2.9 mg, 0.019 mmol), sodium hypochlorite (3.4 mg, 0.038 mmol) and 2-methyl-2-butene (0.013 mL, 0.126 mmol) were added at room temperature, and the mixture was stirred at the same temperature for one hour. A saturated aqueous potassium bisulfate aqueous solution and ethyl acetate were added to the reaction mixture. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=2/1) to give the title compound (1.2 mg, 7%).

Provenance & Evidence