Potassium Carbonate → (5,6-Dioxo-2,3,5,6-tetrahydronaphtho[1,2-b][1,4]oxathiin-2-yl)methyl (4-fluorophenyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(hydroxymethyl)-2,3-dihydronaphtho[1,2-b][1,4]oxathiine-5,6-dione (0.13 g, 0.50 mmol) in N,N-dimethylformamide (1.5 mL) was added 1-fluoro-4-isocyanatobenzene (0.024 mL, 0.55 mmol) and potassium carbonate (0.026 g, 0.50 mmol). The mixture was stirred at 40° C. for 3 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The crude mixture was purified by flash column chromatography (SiO2, 10% methanol in EtOAc) to give the product as a purple solid (0.051 g, 26%). M.p.=235-237° C.; 300 MHz 1H NMR (DMSO-d6) δ: 9.89 (s, 1H), 7.89 (d, J=7.5, 1H), 7.71 (br. s, 2H), 7.50 (m, 3H), 7.12 (m, 2H), 4.78 (m, 1H), 4.53 (m, 2H), 3.18 (m, 2H); LCMS: 400 [M+H].

Provenance & Evidence