Methanol → HCID 71468391, compound

Participants

Reaction Steps

A solution of 1-{4-[1-(cyclopropylmethyl)-4-ethenyl-1H-benzotriazol-5-yl]benzyl}-3-methylimidazolidine-2,4-dione [(Example 19, Step 1), 328 mg, 0.817 mmol] in methanol (8.2 mL) and dichloromethane (24.5 mL) was cooled to −78° C. Ozone was bubbled through the mixture until saturated and then removed. Oxygen was bubbled through the solution for 15 minutes and then treated with polymer-bound triphenylphosphine (0.27 g, 3 mmol/g). The mixture was warmed to ambient temperature and stirred for 14 hours. The mixture was filtered and the solid was washed with methanol. The filtrate was concentrated in vacuo and purified via silica gel chromatography (ethyl acetate/hexane gradient), providing the titled compound: 1H NMR (400 MHz, CDCl3) 10.39 (s, 1H), 7.86 (d, 1H, J=8.4 Hz), 7.55 (d, 1H, J=8.8 Hz), 7.45 (d, 2H, J=8.2 Hz), 7.39 (d, 2H, J=8.2 Hz), 4.67 (s, 2H), 4.62 (d, 2H, J=6.8 Hz), 3.83 (s, 2H), 3.09 (s, 3H), 1.40-1.46 (m, 1H), 0.67-0.72 (m, 2H), 0.51-0.55 (m, 2H) ppm. LRMS m/z (M+H) 404.2 found, 404.2 required.

Provenance & Evidence