m-Chloroperbenzoic acid → HCID 59854957, compound

Participants

Reaction Steps

To a solution of 20 mg (0.044 mmol) of 3-1 in 1 mL of CH2Cl2 at 0° C. was added 11 g (˜0.048 mmol) of mCPBA. The ice-bath was removed and the reaction was stirred for 30 min. The mixture was partitioned with EtOAc and saturated aqueous NaHCO3, separated, washed with H2O, brine, dried over Na2SO4 and concentrated by rotary evaporation. The residue was loaded onto a silica gel column and eluted with EtOAc—20:1:1 EtOH/NH4OH/H2O to provide 9-1 as a white foam. Data for 9-1: 1HNMR (500 MHz, CDCl3) δ 7.4-7.2 (m, 5H), 7.1-6.9 (nm, 3H), 6.25 (s, 1H), 5.0-4.9 (m, 2H), 4.7. (m, 1H), 4.5 (m, 1H), 4.3-4.2 (m, 1H), 4.0 (m, 2H), 3.7 (m, 1H), 3.4-3.3 (m, 2H), 3.3 (s, 3H), 3.2 (s, 3H), 2.5-1.9 (bs, 2H), 1.8 (m, 1H) ppm. HRMS (ES) calc'd M+H for C25H28F3N3O3: 476.2156. Found: 476.2165.

Provenance & Evidence