Dimethylformamide → HCID 69478080, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-deoxy-2-fluorocytidine (0.32 g, 1.32 mmol) and DMAP (0.32 g, 2.60 mmol) in 5.0 mL of anhydrous DMF was added Et3N (0.27 mL, 1.95 mmol) and TBDPSCl (0.50 mL, 1.96 mmol) at 0° C. under N2 atmosphere. The resulting solution was stirred for 12 h at 50° C. and treated with MeOH (0.5 mL) at rt. After stirring the solution additionally, the solvent was removed under reduced pressure. The residue was dried under high vacuum for 24 h at room temperature. The crude product was dissolved in 10 mL of anhydrous pyridine at 0° C. under N2 atmosphere. To the solution was added to benzoyl chloride (0.4 mL, 3.40 mmol). After stirring the solution at rt for 12 h, the solution was treated with MeOH (1.0 mL) at rt. The solution was concentrated in vacuo and the residue was purified on silica gel column chromatography (Hexane:EtOAc=2:1 to 1:2 v/v) to give compound 2 (0.64 g, 0.92 mmol) in 82% yield. 1H NMR (CDCl3, 400 MHz) δ 9.31 (br, 1H), 8.45 (d, J=8.0, 1H), 7.96 (m, 4H), 7.66-7.37 (m, 15H), 7.18 (m, 2H), 6.26 (d, J=16.0, 1H), 5.50 (m, 1H), 5.48 (d, J=3.5, 0.5H), 5.34 (d, J=3.5, 0.5H), 4.52 (d, J=8.8, 1H), 4.28 (dd, J=12.0, 1.6, 1H), 3.87 (dd, J=12.0, 1.6, 1H), 1.10 (s, 9H); MS calcd for C39H38FN3O6Si m/z 692.3 (M+H)+, found 692.4.

Provenance & Evidence