Dimethylformamide → HCID 178452941, compound

Participants

Reaction Steps

Potassium carbonate (1.45 g, 10.50 mmol) is added to 1H-1,2,4-triazole-3-thiol (424.79 mg, 4.20 mmol) and dimethylformamide (10.50 mL, 9.93 g, 135.80 mmol) at room temperature and stirred. After 5 minutes, di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (1.40 g, 2.10 mmol) is added to the reaction and stirred at 85° C. After 2 days, cool the reaction to room temperature, dilute with saturated sodium bicarbonate, then extract with ethyl acetate (3×). The combined organics are washed with water, brine, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography eluting with 5-75% ethyl acetate in hexanes to give the title compound (978.0 mg, 1.46 mmol, 69%). MS (m/z): 671/669 (M−1).

Provenance & Evidence