Ammonia → Tiazofurin

Participants

Reaction Steps

Ethyl 2-(5′-O-Benzoyl-β-D-ribofuiranosyl)thiazole-4-carboxylate (11, 3.7 g, 942 mmol) was placed in a steel bomb and mixed with freshly prepared cold methanolic ammonia (70 ml, saturated at 0° C. The mixture was protected from moisture and stirred at room temperature for 12 hr. The steel bomb was cooled to 0° C., opened carefully and evaporated to a sticky foam. The residue was triturated with dry toluene (3×50 ml) and the toluene layer was discarded. The residue that obtained was treated with anhydrous ethanol (60 ml) and triturated to give light yellow solid. The solid was filtered, washed with ethyl acetate and dried. The solid was crystallized from ethanol-ethyl acetate to provide 2.25g (90%) of pure product: mp 145-147° C. 1H NMR (DMSO-d6): δ 3.57 (M,2 H), 3.89) (s,2 H), 4.07(m, 1 H), 4.83 (t, 1H), 4.92 (d, 1H), 5.05 (d, 1 H), 5.36 (d, 1 H), 7.56 (s, 1), 7.69 (s, 1) and 8.20 (s,1).

Provenance & Evidence