Hydrogen Peroxide → HCID 135526540, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 0.52 mL, ca. 10.4 mmol) was added dropwise to a stirred solution of TFAA (1.5 mL, 10.4 mmol) in DCM (15 mL) at 0° C. The solution was stirred at 0° C. for 5 min, warmed to 20° C. for 10 min, then cooled to 0° C. and added to a stirred solution of 1-oxide 26 (312 mg, 1.0 mmol) and TFA (0.40 mL, 5.2 mmol) in DCM (20 mL) at 0° C. The solution was stirred at 5° C. for 4 h, diluted with dilute aqueous NH3 solution (10 mL) and extracted with CHCl3 (4×50 mL). The combined organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1,4-dioxide 27 (179 mg, 54%) as a red gum: 1H NMR δ 8.11 (br s, 2H, H-5, H-9), 7.73 (br s, 1H, NH), 3.64-3.69 (m, 2H, CH2N), 3.01-3.10 (m, 4H, H-6, H-8), 2.81-2.85 (m, 2H, CH2N), 2.64-2.73 (m, 4H, 2×CH2N), 2.14-2.22 (m, 2H, H-7), 1.09 (t, J=7.1 Hz, 6H, 2×CH3); 13C NMR δ 156.0, 149.5, 145.8, 138.1, 129.8, 115.7, 111.7, 51.1, 46.6 (2), 38.5, 33.4, 32.3, 25.6, 11.0 (2); MS (FAB+) m/z 318 (MH+, 70%), 302 (20); HRMS (FAB+) calcd for C16H24N5O2 (MH+) m/z 318.1930, found 318.1933.

Provenance & Evidence