Ammonia → HCID 54010489, compound

Participants

Reaction Conditions

Reaction Steps

Compound 31 (6.0 g, 9.5 mmol) was dissolved in MeOH/NH3 (dry MeOH sat. with anhydrous NH3 at 0° C., 60 mL) were placed in a steel reaction vessel. The vessel was heated at 95° C. for 16 h. The reaction vessel was cooled, opened carefully and the NH3 was allowed to evaporate at room temperature. The MeOH was evaporated to dryness and the residue was triturated with hot toluene (3×50 mL) and filtered. The brown residue was crystallized from aqueous EtOH (95%) to furnish 2.40 g (89%) of 32: mp 210-212° C.; 1H NMR (Me2SO-d6) δ 3.45-3.59 (m, 2H, C5′H), 3.98 (m, 1H, C4.H), 4.25 (m, 1H, C3.H), 4.54 (m, 1H, C2′H), 4.78 (t, 1H, C5′OH, D2O exchangeable), 5.27 and 5.67 (2d, 2H, C2′,3′OH, D2O exchangeable), 5.89 (d, 1H, J1′,2′=3.85 Hz, C1′H), 8.05 and 9.05 (2br s, 4H, 2 CONH2). Anal. CaIc. for C9H13N5O6 (287.23): C, 37.63; H, 4.56; N, 24.38. Found: C, 37.52; H, 4.19; N. 24.59.

Provenance & Evidence