Ethylacetate methanol → HCID 135477942, compound

Participants

Reaction Steps

Oxidation of 1-oxide 24 (829 mg, 2.6 mmol) with CF3CO3H (ca. 26.1 mmol) gave (i) starting material 24 (270 mg, 32%) and (ii) 1,4-dioxide 25 (206 mg, 24%) as a red solid, mp (MeOH/EtOAc) 142-144° C.; 1H NMR δ 8.55 (br s, 1 H, NH), 8.22 (d, J=9.0 Hz, 1 H, H-8), 8.10 (d, J=1.7 Hz, 1 H, H-5), 7.31 (dd, J=9.0, 1.7 Hz, 1 H, H-7), 3.82-3.87 (m, 4 H, 2×CH2O), 3.66-3.72 (m, 2 H, CH2N), 2.86 (q, J=7.6 Hz, 2 H, CH2), 2.58 (br dd, J=6.2, 6.0 Hz, 2 H, CH2N), 2.49-2.55 (m, 4 H, 2×CH2N), 1.85-1.92 (m, 2 H, CH2), 1.35 (t, J=7.6 Hz, 3 H, CH3); 13C NMR δ 153.9, 150.0, 138.5, 128.8, 128.2, 121.5, 114.9, 66.9 (2), 57.8, 53.9 (2), 41.7, 29.5, 24.4, 14.5. Anal. Calcd for C15H23N5O3: C, 57.6; H, 7.0; N, 21.0. Found: C, 57.6; H, 6.9; N, 20.9%

Provenance & Evidence