Ethyl Acetate → HCID 131728573, compound

Participants

Reaction Steps

The above-obtained 3′,5′-bis-O-(tert-butyldimethylsilyl)-2-N-methylcarbamoyldeoxyguanosine (889 mg, 1.61 mmol) was azeotroped with anhydrous pyridine three times and then dissolved in anhydrous pyridine (16 mL), and diisopropylethylamine (421 μL, 2.41 mmol) and then diphenylcarbamoyl chloride (424 mg, 1.93 mmol) were added thereto. The mixture was stirred at room temperature for 0.5 hours. Then, after addition of ethyl acetate (10 mL), the reaction was terminated by adding sodium bicarbonate water (10 mL) thereto. The reaction solution was extracted with ethyl acetate (150 mL)/sodium bicarbonate water (150 mL) once and then with ethyl acetate (150 mL)/brine (100 mL) twice. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (C200) with ethyl acetate/40% to 50% hexane to give 3′,5′-bis-O-(tert-butyldimethylsilyl)-6-O-diphenylcarbamoyl-2-N-methylcarbamoyldeoxyguanosine (1.13 g, 94%).

Provenance & Evidence