Ammonia → 2',3'-Didehydro-2',3'-dideoxycytidine
Reaction equation
C([NH:4][C:5]1[CH:17]=[CH:16][N:8]([C@@H:9]2[O:15][C@H:12]([CH2:13][OH:14])[CH:11]=[CH:10]2)[C:7](=[O:18])[N:6]=1)(=O)C.N>CO>[C@@H:9]1([N:8]2[CH:16]=[CH:17][C:5]([NH2:4])=[N:6][C:7]2=[O:18])[O:15][C@H:12]([CH2:13][OH:14])[CH:11]=[CH:10]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 33 (0.26 g, 1.03 mmol) in methanol saturated with ammonia (20 ml) was stirred at 45°-50° C. for 12 hours. The solvent was removed under reduced pressure. The residue was triturated with isopropanol, filtered, and then washed with isopropanol to yield 0.15 g (69%) of 3: mp 167°-169° C. (benzene-methanol) (Lit. mp 168°-169° C.); 1H NMR (DMSO-d6) δ 3.51 (2H, m, 5'-H), 4.75 (1H, m, 4'OH), 4.85 (1H, t, J=5.5 Hz, OH), 5.68 (1 H, d, J=7.3 Hz, 5-H), 5.85 (1H, br d, J=5.9 Hz, 2'-H), 6.35 (1H, br d, J=5.9 Hz, 3'-H), 6.89 (1H, m, 1'-H), 7.10 (2H, s, NH2), 7.67 (1H, d, J=7.3 Hz, 6-H).