Hydrogen Peroxide → HCID 71006908, compound

Participants

Reaction Steps

Trifluoromethyliodide gas was bubbled through 4 mL of dimethylsulfoxide for 3 min at rt. In this way, approximately 0.9 g of trifluoromethyliodide was dissolved in this solution. Dicyclopentadienyliron(II) (21.9 mg, 0.114 mmol) and tert-butyl (4R,7S,8S)-7-(2,3-difluorophenyl)-4-hydroxy-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-8-ylcarbamate (45.3 mg, 0.114 mmol) was dissolved in 2 mL of the trifluoromethyliodide-dimethylsulfoxide solution described above. Hydrogen peroxide (0.012 mL, 0.114 mmol) was added to the reaction mixture. The reaction was stirred at rt for 1 h. Aqueous sodium carbonate was added and the reaction was extracted with ethyl acetate. The ethyl acetate layer was washed with water (2×) and dried (sodium sulfate). The product was purified by flash chromatography, eluting with ethyl acetate in hexane from 0 to 30% to 45% to give the desired product (12.5 mg, 24%): LCMS (M+H=465.08); 1H NMR (400 MHz, CHLOROFORM-d) δ 7.21-6.97 (m, 3H), 5.30-5.16 (m, 1H), 498-4.84 (m, 2H), 3.43-3.28 (m, 1H), 3.12-2.79 (m, 2H), 2.43-2.13 (m, 3H), 1.37-1.18 (m, 9H).

Provenance & Evidence