Uracil → HCID 57867363, compound

Participants

Reaction Steps

To a stirred solution of uracil (about 0.30 g, 2.71 mmol) in acetonitrile (about 7 ml) was added N,O-Bis(trimethylsilyl)acetamide at room temperature (about 4 ml, 16.3 mmol) and refluxed for about 2 hours. To this added ((2R,4R)-3,5-diacetoxy-4-fluoro-3,4-dimethyl-tetrahydrofuran-2-yl)methyl benzoate (about 0.5 gm, 1.35 mmol) in acetonitrile (about 8 ml) drop wise at about 0° C., and added SnCl4 (about 0.2 ml, 2.03 mmol) and refluxed for about 15 hours, Completion of the reaction monitored by thin-layer chromatography and neutralized the reaction mixture with saturated sodium bicarbonate solution. Aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine and dried over sodium sulphate. Concentration under reduced pressure and purification by silica gel column chromatography using 35% ethyl acetate/hexane as eluent furnished title compound (0.35 g) as a colorless solid. Yield: 61%; 1H-NMR: 1H NMR (300 MHz, CDCl3): δ 8.67 (s, 1H), 8.06-8.03 (m, 2H), 7.59-7.33 (m, 4H), 6.39 (d, 1H, J=22.8 Hz), 5.76, 5.55 (dd, 1H, J=2.1 Hz, J=2.4 Hz), 4.80-4.43 (m, 3H), 2.13 (s, 3H), 1.81 (d, 3H, J=2.4 Hz), 1.49 (d, 3H, J=23.4 Hz); ES Mass: [M+Na] 443 (100%); IR cm−: 3433, 2931, 2346, 1713, 1385, 1274, 952, 712; HPLC: 96%.

Provenance & Evidence