Water → HCID 14503094, compound

HRID 1494510Notes

Reaction equation

HRID 1494510 reaction equation
[C@@H:1]1([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[S:19][NH2:20])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].O.ClC1C=C(C=CC=1)C(OO)=[O:27]>C(O)C>[C@@H:1]1([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[S:19]([NH2:20])=[O:27])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 14503090HCID 14503090, compound

Product 1

HCID 14503094HCID 14503094, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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.

Workup

  1. filtrationAfter 4 h the separated crystals were filtered off
  2. customthe filtrate was evaporated to dryness
  3. customtriturated with methanol
  4. filtrationfiltered
  5. washwashed with methanol
  6. customdried at room temperature

Sources & evidence

ORD record
ord-0692509cb3464505b729beed19a7c78c
Source dataset
uspto-grants-1991_06
Patent number
US05026836

Reaction notes

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