Hydrogen Peroxide → HCID 21825595, compound

HRID 917826Notes

Reaction equation

HRID 917826 reaction equation
[C:1]([C:3]1[CH:7]=[N:6][N:5]([C@@H:8]2[O:20][C@H:19]([CH2:21][O:22]C(=O)C)[C@@H:14]([O:15]C(=O)C)[C@H:9]2[O:10]C(=O)C)[N:4]=1)#[N:2].[OH:26]O>[Pt].N>[C@@H:8]1([N:5]2[N:4]=[C:3]([C:1]([NH2:2])=[O:26])[CH:7]=[N:6]2)[O:20][C@H:19]([CH2:21][OH:22])[C@@H:14]([OH:15])[C@H:9]1[OH:10]

Participants

5

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 21825597HCID 21825597, compound

Product 1

HCID 21825595HCID 21825595, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 222AmmoniaSolvent

Procedure

4-Cyano-2-(2,3,5-tri-O-acetyl-β -D- ribofuranosyl)-1,2,3-triazole (7) (0.35 g, 0.001 mol) was added to 15% aqueous ammonia (30 ml) and 30% hydrogen peroxide (3 ml). After stirring at room temperature for 6 hr an additional 3 ml of 30% hydrogen peroxide was added and stirring was continued for 20 hr. Platinum black was added to destroy the excess peroxide, the solution was filtered, and the filtrate was evaporated to dryness. The residue was dissolved in a minimum of methanol and applied to a 20 × 20 cm silica gel preparative plate which was developed in ethyl acetate-methanol (9:1). The band containing 4 was removed and the compound was extracted with ethyl acetate-methanol (1:1). The solvent, along with acetamide, was removed in vacuo. The compound was dissolved in hot 2-propanol; cooling of the solution and filtering provided 14 mg of 4.

Workup

  1. additionwas added
  2. customto destroy the excess peroxide
  3. filtrationthe solution was filtered
  4. customthe filtrate was evaporated to dryness
  5. dissolutionThe residue was dissolved in a minimum of methanol
  6. additionThe band containing 4
  7. customwas removed
  8. extractionthe compound was extracted with ethyl acetate-methanol (1:1)
  9. customThe solvent, along with acetamide, was removed in vacuo
  10. dissolutionThe compound was dissolved in hot 2-propanol
  11. temperaturecooling of the solution
  12. filtrationfiltering

Sources & evidence

ORD record
ord-aa1fe4ef0aea4644a26d04f47d220455
Source dataset
uspto-grants-1976_07
Patent number
US03968103

Reaction notes

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