Cesium carbonate → HCID 178429687, compound

Participants

Reaction Conditions

Reaction Steps

Di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-methylsulfonyloxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate (5.3 g, 8.21 mmol) is dissolved in dimethylformamide (100 mL). To this mixture is added cesium carbonate (5.40 g, 16.41 mmol), 1H-1,2,4-triazole-3-thiol (3.42 g, 32.83 mmol), and sodium triacetoxyborohydride (906 mg, 4.10 mmol). The mixture is stirred at 40° C. for 72 hours. The reaction is cooled and quenched with water and aqueous NH4Cl. The mixture is transferred to a separatory funnel and extracted with diethyl ether, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography (0 to 50% ethyl acetate/hexanes) to give the title compound (0.88 g, 1.35 mmol, 16.5% yield). MS (m/z): 651 (M+H).

Provenance & Evidence