Water → HCID 14503094, compound

Participants

Reaction Steps

To an ice cooled stirred solution of 10 (1.5 g, 5 mmol) in ethanol:H2O (525 mL, 20:1, v/v), m-chloroperoxybenzoic acid (1 g, 1 eq.) in ethanol (50 mL) was added dropwise during 20 min. After 4 h the separated crystals were filtered off, the filtrate was evaporated to dryness, triturated with methanol, filtered, washed with methanol and dried at room temperature to yield 11, (0.5 g, 31% yield), m.p. >120° C. The filtrate was evaporated and purified by chromatography as described for 6 to yield another crop of 11, (0.25 g, 15%: overall yield 46%). IR (KBr): 1060 (vs, br, S=O), 1330 (s, S=O), 3000-3600 (NH2, OH) cm-1 : UV: λmax (pH 1) 272 nm (ε 3,000): λmax (pH 7) 275 nm (ε7,100): λ max (pH 11) 272 nm (ε 1,700): 1H NMR (DMSO-d6): δ 6.46 (d, 1, J =5.16 Hz, C1'H), 6.71 (s, 2, SONH2, exchanged with D2O), 8.83 (s, 1, C2H), 9.06 (s, 1, C8H), and other sugar protons. Anal. Calcd for C10H13N5O5S·0.3H2O (321.32): C, 37.38: H, 4.24: N, 21,80: S, 9.97. Found: C, 37.03: H, 4.19: N, 21.42: S, 10.37.

Provenance & Evidence