Cesium carbonate → HCID 59619302, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1R,2R,4R)-2-(3,3-Difluoro-azetidine-1-carbonyl)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (Example 118, 87 mg, 0.16 mmol), cesium carbonate (162 mg, 0.49 mmol) and 3-hydroxyoxetane (35 mg, 0.5 mmol) in N,N-dimethylformamide (3 mL) was stirred at 50° C. for 16 h. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogenocarbonate. The aqueous layer was extracted with ethyl acetate then the combined organic layers were washed with water and brine then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of dichloromethane/methanol (98:2 v/v) as eluant to afford the title compound (34 mg, 35%) as a white solid. MS (EI): 578.13 (M+H)+.

Provenance & Evidence