Acetic Anhydride → Ribavirin 2',3',5'-triacetate

HRID 1703734Notes

Reaction equation

HRID 1703734 reaction equation
[C@@H:1]1([N:10]2[CH:14]=[N:13][C:12]([C:15]([NH2:17])=[O:16])=[N:11]2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3].C(O[C:22](=[O:24])[CH3:23])(=O)C>N1C=CC=CC=1>[C:2]([O:3][C@@H:2]1[C@H:4]([O:5][C:4](=[O:5])[CH3:6])[C@@H:6]([CH2:8][O:9][C:22](=[O:24])[CH3:23])[O:7][C@H:1]1[N:10]1[CH:14]=[N:13][C:12]([C:15]([NH2:17])=[O:16])=[N:11]1)(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 37542Ribavirin

Product 1

HCID 3080793Ribavirin 2',3',5'-triacetateYield 75.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-(β -D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (488 mg., 2.00 mmol) in pyridine (10.0 ml.) containing acetic anhydride (1.0 ml.) was added and the solution was stirred at room temperature for 2 hrs. The solvent was removed and water was added to the residue. The mixture was extracted with methylene chloride (three 20-ml. portions) and the organic layer was extracted with aqueous sodium hydrogen carbonate and water. The organic phase was dried over magnesium sulfate, filtered, and evaporated to a syrup which was applied to a silica gel column. Elution with chloroform-methanol (19:1) provided the pure product as an amorphous solid (560 mg., 75.6%).

Workup

  1. additionwas added
  2. customThe solvent was removed
  3. additionwater was added to the residue
  4. extractionThe mixture was extracted with methylene chloride (three 20-ml. portions)
  5. extractionthe organic layer was extracted with aqueous sodium hydrogen carbonate and water
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to a syrup which
  9. washElution with chloroform-methanol (19:1)

Sources & evidence

ORD record
ord-4c7735963a6e4f39a179cfd15766ee6a
Source dataset
uspto-grants-1978_11
Patent number
USRE029835

Reaction notes

Loading…