Cesium carbonate → HCID 71008442, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2R,6S,13aS,14aR,16aS,Z)-ethyl 2-(4-bromophenylsulfonyloxy)-6-(tert-butoxycarbonylamino)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (1b, 2.3 g, 3.2 mmol), 3-fluorophenanthridin-6-ol (Example 1a, 0.688 g, 3.23 mmol) and cesium carbonate (1.2 g, 3.6 mmol) in dimethylformamide (32 ml) was heated @80° C. for 5 h. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and 2 N HCl. The organic phase was washed with water and then saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and evaporated. The resulting solid was purified by flash chromatography on silica gel, eluting with acetone/hexane, to provide the title compound (1.3 g, 60% yield).

Provenance & Evidence