Hydrochloric Acid → HCID 45380783, compound

Participants

Reaction Steps

To a solution of 5-[4-fluoro-2-(trifluoromethyl)phenyl]-4-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide (23 g, 52 mmol) in anhydrous DMA (160 ml) was added sodium tert-butoxide (12 g, 0.12 mol) and stirred at room temperature for 30 min under N2. (4S,5S)-4,5-dimethyl-1,3,2-dioxathiolane 2,2-dioxide (12 g, 78 mmol) in anhydrous DMA (20 ml) was added to the solution and stirred at 70° C. for 2.0 h. The reaction mixture was cooled to room temperature and added 2N HCl (80 ml) and concentrated on a rotary evaporator. To this residue was added anhydrous THF (0.12 L) and 5N HCl (0.14 L) and stirred at 60° C. for 80 min. The mixture was diluted with ethyl acetate and washed with water, satd NaHCO3 and brine, then dried over sodium sulfate and concentrated on a rotary evaporator. The resulting residue was purified by silica-gel column chromatography (1:2, dichloromethane:ethyl acetate) to give an atropisomeric mixture of the title compound (14.3 g, 52%) as a pale yellow solid.

Provenance & Evidence