Imidazole → HCID 54282809, compound

Participants

Reaction Steps

An aqueous solution of hydrogen fluroride (46%, 2.53 ml) was added to a solution of the compound (2.29 g, 5.8 mmol) prepared in Example 7 in acetonitrile (40 ml) at room temperature in an argon atmosphere. After stirring for two hours at this temperature, the mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a de-protected compound as an oily substance. Imidazole (579 mg, 8.5 mmol) and triethylsilyl chloride (1.24 ml, 7.4 mmol) were added to the solution of this de-protected compound in N,N-dimethylformamide (10 ml) at room temperature, followed by stirring for 10 minutes at the same temperature. After the reaction, the reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of potassium hydrogen sulfate, a saturated aqueous solution of sodium hydrogencarbonate, and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1), to obtain 1.52 g (yield 67%) of the title compound as a light yellow oily substance.

Provenance & Evidence