Hydrogen Peroxide → Ribavirin

HRID 1703730Notes

Reaction equation

HRID 1703730 reaction equation
[C:1]([C:3]1[N:7]=[CH: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>N>[C@@H:8]1([N:5]2[CH:6]=[N:7][C:3]([C:1]([NH2:2])=[O:26])=[N:4]2)[O:20][C@H:19]([CH2:21][OH:22])[C@@H:14]([OH:15])[C@H:9]1[OH:10]

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 134568011-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carbonitrile

Product 1

HCID 37542RibavirinYield 51.2%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A mixture of 3-cyano-1-(2,3,5 -tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazole (705 mg., 2.0 mmole), 28% aqueous ammonia (20 ml.) and 30% hydrogen peroxide (3.0 ml.) was stirred at 25° for 6 hrs. An additional 3.0 ml. portion of 30% hydrogen peroxide was then added and stirring at 25° was continued for 12 hrs. The excess hydrogen peroxide was destroyed by addition of platinum black, the solution was filtered, the filtrate was evaporated to dryness. The residue was dissolved in methanol and silic gel (5.0 g.) was added to the solution. The solvent was removed and the silica gel mixture was applied to a silica gel column. Elution with ethyl acetate-methanol (1:1) provided 1-(β -D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (250 mg., 51.2%).

Workup

  1. stirringstirring at 25°
  2. waitwas continued for 12 hrs
  3. customThe excess hydrogen peroxide was destroyed by addition of platinum black
  4. filtrationthe solution was filtered
  5. customthe filtrate was evaporated to dryness
  6. dissolutionThe residue was dissolved in methanol
  7. additionsilic gel (5.0 g.) was added to the solution
  8. customThe solvent was removed
  9. washElution with ethyl acetate-methanol (1:1)

Sources & evidence

ORD record
ord-f52a1464bfaa410fb04c27213ee71b55
Source dataset
uspto-grants-1978_11
Patent number
USRE029835

Reaction notes

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