N4-Acetyl-2',3'-didehydro-2',3'-dideoxycytidine → N4-Acetyl-2',3'-dideoxycytidine

Participants

Reaction Steps

A solution of 33 (0.78 g, 3.1 mmol) in ethanol (100 mL) was hydrogenated under 15 psi of hydrogen gas in the presence of 10% Pd/C (0.15 g) for 12 hours. The reaction mixture was filtered, concentrated, and the residue was purified by chromatography over silica using 5% methanol in CHCl3 as the eluent to obtain 0.61 g (77.5%) of 34 as a colorless solid: mp 143°-145° C. (benzene-methanol); 1H NMR (DMSO-d6) δ 1.60-2.50 (7H, m, 2',3'-H and COCH3), 3.40-3.85 (2H, m, 5'-H), 3.90-4.30 (1H, m, 4'-H), 5.07 (1H, t, J=5.0 Hz, OH), 5.91 (1H, m, 1'-H), 7.17 (1H, d, J=7.6 Hz, 5-H), 8.32 (1H, d, J=7.3 Hz, 6-H), 10.80 (1H, s, NH).

Provenance & Evidence