Triethylammonium hydroxide → HCID 89852256, compound

Participants

Reaction Steps

To a solution of (2S,5R)-6-(allyloxy)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (Intermediate 16, 146 mg, 0.62 mmol) in DCM (6 mL), under nitrogen, at room temperature was added methoxycarbonylsulfamoyl)triethyl-ammonium hydroxide inner salt (Burgess Reagent) (660 mg, 2.77 mmol) portionwise over 2 hours. The reaction was stirred at room temperature for an additional 30 minutes. The reaction mixture was washed with 1:1 brine:water. The organic layer was dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-25% ethyl acetate/hexanes) afforded (2S,5R)-6-(allyloxy)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carbonitrile (112 mg, 83%) as a colorless oil.

Provenance & Evidence