m-Chloroperbenzoic acid → HCID 14503106, compound

Participants

Reaction Steps

A solution of 49 (1.5 g, 4.7 mmol) in ethanol (350 mL) and water (50 mL) was cooled to 0° C. To this cold solution was added m-chloroperoxybenzoic acid (80%, 0.90 g, 4.45 mmol) in ethanol (50 mL) during 1.5 h. After the addition, the reaction mixture was stirred at ice-bath temperature for 1.5 h. The solvent was evaporated under reduced pressure and the residue was dissolved in methanol (50 mL). Silica gel (≈5 g) was added and evaporated to dryness. The dried silica gel was placed on top of a flash silica gel column and the column was eluted with ethyl acetate→methanol gradient. The pure compound crystallized out after concentration of the homogeneous fractions. The product was collected by filtration and dried to give 0.95 g (60%) of the title compound, mp >200° C. (dec.): IR (KBr): 1120 (S=O), 3100-3600 (NH2, OH)cm-1 : UV: λmax (pH 1) 220 nm (ε17,900), 249 (7,600), 330 (5,100): λmax (pH 7) 225 nm (ε24,100), 248 (sh) (6,100), 323 (8,000): λmax (pH 11) 224 nm (ε 21,000), 244 (sh) (6,600), 322 (6,600): 1H NMR (DMSO-d6): δ 6.17 (d, J 4.08 Hz, C1'H), 6.50 (s, 2, SONH2, exchanged with D2O), 6.97 (s, 2, NH2, exchanged with D2O), 8.25 (s, 1, C8H), and other sugar protons. Anal. Calcd. for C10H14N6O5S (330.32): C, 36.36; H, 4.27; N, 25.44; S, 9.71. Found: C, 36.65; H, 4.09; N, 25.19; S, 9.56.

Provenance & Evidence