Water → HCID 131728914, compound

Participants

Reaction Conditions

Reaction Steps

Water (1.4 mL) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (831 mg, 3.66 mmol) were added to a methylene chloride solution (25 mL) of tert-butyl(±)-[(1R,5R,6R)-6-{[(tert-butoxycarbonyl)amino]methyl}-3-{[(4-methoxybenzyl)oxy]methyl}bicyclo[3.2.0]hept-3-en-6-yl]acetate (1.19 g, 2.44 mmol) with stirring at 0° C. The mixture was stirred at this temperature 0° C. for 1 hour and further stirred at room temperature for 1 hour. Then, the reaction was terminated by the addition of a saturated aqueous solution of sodium bicarbonate, followed by extraction with methylene chloride. The organic layer was washed with water, a saturated aqueous solution of sodium bicarbonate, and saturated saline and dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (571 mg, 64%).

Provenance & Evidence