Hydroxylamine HCl → HCID 136331249, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the compound (501 mg, 1.50 mmol) obtained in Example 18b in dimethylsulfoxide (5 mL) were added hydroxyammonium chloride (1.04 g, 15.0 mmol) and sodium hydrogen carbonate (1.26 g, 15.0 mmol), and the mixture was stirred at 80° C. overnight. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. Tetrahydrofuran (10 mL), 1,1′-carbonyldiimidazole (365 mg, 2.25 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.224 mL, 1.5 mmol) were added to the residue, and the mixture was stirred at room temperature for 2.5 hr, and further heated under reflux for 1.5 hr. The reaction mixture was extracted with ethyl acetate, washed successively with 1N hydrochloric acid and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) and recrystallized from ethyl acetate-hexane to give the title compound (426 mg, 72%) as colorless crystals.

Provenance & Evidence