Acetic Acid → HCID 86592809, compound

Participants

Reaction Steps

To a suspension of 4-chloro-7-fluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo[4,5-c]pyridine (45, 0.73 g, 1.2 mmol) in dry methanol (50 mL) was added sodium methoxide until pH 10 was reached. The reaction mixture was refluxed for 30 min, cooled, neutralized with glacial acetic acid, and evaporated to dryness. The residue was purified by silica gel column chromatography (CH2Cl2/EtOH, 10:1, v/v) to give 0.29 g (78%) as a white solid: mp 187-189° C.; 1H NMR (DMSO-d6) δ3.58 (m, 1 H, 5′-HA), 3.70 (m, 1 H, 5′-HB), 3.99 (m, 1 H, 4′-H), 4.13 (m, 1 H, 3′-H), 4.36 (m, 1 H, 2′-H), 5.16 (t, 1 H, 5′-OH, D2O exchangeable), 5.28 (d, 1 H, OH, D2O exchangeable), 5.63 (d, 1 H, OH, D2O exchangeable), 6.03 (d, 1 H, 1′-H, J=5.1 Hz), 8.27 (d, 1 H, 6-H, J=2.1 Hz), 8.88 (s, 1 H, 2-H). Analysis calculated for C11H11ClFN3O4: C, 43.50; H, 3.65; N, 13.84. Found: C, 43.43; H, 3.26; N, 13.81.

Provenance & Evidence