Water → HCID 86619233, compound

Participants

Reaction Steps

N-{3-[6-(3-Cyano-5-methyl-benzoyl)-5-isopropyl-2,4-dioxo-3,4-dihydro-2 H-pyrimidin-1-ylmethyl]-5-fluoro-phenyl}-2,2,2-trifluoro-N-(4-methoxy-benzyl)-acetamide (389 mg, 0.61 mmol) was dissolved in acetonitrile (6 ml). With stirring, ceric ammonium nitrate (669 mg, 1.2 mmol) and distilled water (3 ml) were added in this order. After 24 hr., the mixture was diluted with ethyl acetate, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexane (1:2)) to afford 240 mg (76%) of a white solid. 1H NMR (200 MHz, DMSO-d6) δ 1.03 (3H, d, J=6.8 Hz), 1.18 (3H, d, J=6.8 Hz), 2.09 (1H, m), 2.32 (3H, s), 4.42 (1H, d, J=16.8 Hz), 4.97 (1H, d, J=16.8 Hz), 6.80 (1H, m), 7.08 (1H, s), 7.31 (1H, m), 7.91 (1H, s), 7.96 (1H, s), 8.16 (1H, s), 11.28 (1H, s), 11.69 (1H, s).

Provenance & Evidence