Trifluoroacetic acid → 3-(4-(3-Fluoroazetidin-3-yl)phenyl)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

Participants

Reaction Steps

To a solution of 250 mg of tert-butyl 3-fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)azetidine-1-carboxylate (Preparation 8) in 2 mL CH2Cl2 was added 1 mL of trifluoroacetic acid. The reaction was stirred overnight under a positive pressure of nitrogen. The reaction was concentrated. The residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted 2× with EtOAc (20 mL). The combined organics were dried over Na2SO4 and condensed to yield 188 mg of a film. TLC shows much more polar spot. The crude product was carried on to the next reactions. MS calculated for (C19H13Cl3F4N2O), 466.00; found 467.9 M+H

Provenance & Evidence