1-(2',3',5'-Tri-o-benzoyl-beta-l-ribofuranosyl)pyridine-4-one-3-carboxamide → 1-beta-l-Ribofuranosylpyridine-4-one-3-carboxamide

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Reaction Steps

Compound 33 (0.5 g, 0.86 mmol) was dissolved in dry methanolic ammonia (50 mL) and stirred for 15 h in a bomb at room temperature. The solution is then concentrated to a small volume and cooled overnight at 4° C. The crystalline product formed was filtered off, washed with cold methanol. The solid was recyrstallized from absolute ethanol to give 0.23 g (87%) of pure product: mp 209-211° C.; 1H NMR (Me2SO-d6) δ 3.60 (m, 2H, C5′H), 3.93 (m, 1H, C4′H), 4.09 (m, 1H, C3′H), 4.34 (m, 1H, C2′H), 5.11 (m, 1H, C5′OH, D2O exchangeable), 5.22 and 5.47 (2m, 2H, C2′,3′OH, D2O exchangeable), 5.84 (d, 1H, J1′,2′=6.3 Hz, C1′H), 7.21 (m, 2H, PhH), 7.64 (m, 2H, PhH and CONH2) and 8.44 (s, 1H, CONH2). Anal. Calc. for C11H14N2O6(270.24): C, 48.89; H, 5.22; N,10.37. Found: C, 48.89; H, 5.42; N, 10.51.

Provenance & Evidence