Hydrochloric Acid → HCID 23001302, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of alcohol from Step B (375 mg, 0.936 mmol) and diphenylphosphoryl azide (0.242 mL, 1.12 mmol) in toluene (3 mL) at 0° C. was added DBU (0.154 mL, 1.03 mmol). The reaction mixture was stirred at 25° C. for 16 hours, then poured onto 10% HCl (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a brown oil. A solution of the oil and sodium azide (66.9 mg, 1.03 mmol) in DMF (3 mL) was heated to 85° C. for 16 hours. The reaction mixture was poured onto saturated sodium bicarbonate (50 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (0→20% ethyl acetate/hexane) to provide the title compound.

Provenance & Evidence