Sodium → HCID 21853339, compound

Participants

Reaction Steps

To a solution of 5-acetamido-2-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-thiadiazol-3-one (4,1.0 g) or 5-acetamido-2-(β-D-ribofuranosyl)-1,2,4-thiadiazol-3-one (7) in anhydrous methanol (50 ml) was added 1N sodium methozide in methanol, till the pH of the solution was 9.0 and the solution was stirred at 30° for several days. After the reaction was complete, the solution was neutralized by stirring for 15 min with Amberlite IRC-50 (H+) resin. The resin was filtered off and the filtrate was evaporated to dryness in vacuo. The residue was chromatographed on a silica gel column (2.5 × 45 cms) using ethylacetate:water:n-propanol (4:2:1), v/v, upper phase). The appropriate fractions were pooled, solvent evaporated and the reisdue crystallized from aaueous ethanol to yield 0.24 g (40.2%), m.p. > 240° (dec.); 1H nmr (Me2SO-d6) δ5.63 (d, J=4.5 Hz, C1'H); uv λmax (pH 1) 220 nm (ε 14,950), 273 (5000); λmax (pH 7) 220 nm (ε 13,950), 255 (6250); λmax (pH 11) 230 nm (ε 1,200), 278 sh (7500).

Provenance & Evidence