Trimethylamine oxide → HCID 25051365, compound

Participants

Reaction Steps

To a solution of 1-(3,4-dichlorobenzyl)-3-(4-(allyloxymethyl)thiazol-2-yl)urea (Example 90, 100 mg, 0.27 mmol) in a mixture of acetone/water 10/1 (2 ml) was added TMANO (trimethylamine N-oxide, 45 mg, 0.40 mmol) and a OsO4 solution (4% in water, 0.34 mL, 5.4 μmol). The mixture was stirred at room temperature for 3 h and a saturated NaHCO3 solution was added. The solution was extracted with EtOAc (2×25 mL) and the combined extracts were dried over Na2SO4, filtered, and concentrated in vacuo to afford 100 mg of an off-white solid. Purification by column chromatography (SiO2, DCM/4% 7N NH3 in MeOH). 1H-NMR (300 MHz, CDCl3): δ 7.34 (s, 1H), 7.33 (d, 1H), 7.08 (d, 1H), 7.05 (bs, 1H), 6.62 (s, 1H), 4.38 (s, 2H). 4.33 (d, 2H), 3.86 (t, 1H), 3.62-3.50 (m, 4H).

Provenance & Evidence