Hydrogen Peroxide → HCID 135899476, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 0.38 mL, ca. 2.8 mmol) was added dropwise to a stirred solution of TFAA (1.1 mL, 2.8 mmol) in DCM (15 mL) at 0° C. The solution was stirred at 20° C. for 10 min, then cooled to 0° C., added to a solution of 1-oxide 209 (235 mg, 0.78 mmol) and TFA (0.13 mL, 1.7 mmol) in CHCl3 (15 mL) at 0° C. The solution was stirred at 20° C. for 4 h, diluted with dilute aqueous NH3 solution until basic and extracted with CHCl3 (3×25 mL). The combined organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (5-10%) of MeOH/DCM, to give 1,4-dioxide 210 (95 mg, 38%) as a red solid: mp 187-190° C.; 1H NMR (CD3OD) δ 8.16 (t, J=1.7 Hz, 1H, H-9), 7.30 (s, 1H, H-5), 4.85 (t, J=8.4 Hz, 2H, H-7), 3.90-3.94 (m, 2H, CH2), 3.40-3.49 (m, 4H, H-8, CH2), 3.36 (q, J=7.3 Hz, 4H, CH2), 1.37 (t, J=7.3 Hz, 6H, CH3), NH not observed; 13C NMR δ 169.8, 151.5, 142.3, 135.5, 128.2, 119.0, 93.7, 75.6, 51.7, 49.0 (2), 37.3, 29.4, 9.1 (2); HRMS (FAB+) calcd for C15H22N5O3 (MH+) m/z 320.1723, found 320.1726.

Provenance & Evidence