Reaktion #1005008

Reaktionsgleichung

hydrogen peroxide

4-Cyano-2-(2,3,5-tri-O-acetyl-β -D- ribofuranosyl)-1,2,3-triazole

4-cyano-2-(2,3,5-tri-O-acetyl-β -D-ribofuranosyl)-1,2,3-triazole

hydrogen peroxide

→

4

2-β-ribofuranosyl-1,2,3-triazole-4-carboxamide

Lösungsmittel

ammonia

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigeto destroy the excess peroxide
3. 3
   Filtrationthe solution was filtered
4. 4
   Sonstigethe filtrate was evaporated to dryness
5. 5
   workup.DISSOLUTIONThe residue was dissolved in a minimum of methanol
6. 6
   workup.ADDITIONThe band containing 4
7. 7
   Sonstigewas removed
8. 8
   Extraktionthe compound was extracted with ethyl acetate-methanol (1:1)
9. 9
   SonstigeThe solvent, along with acetamide, was removed in vacuo
10. 10
    workup.DISSOLUTIONThe compound was dissolved in hot 2-propanol
11. 11
    Temperaturcooling of the solution
12. 12
    Filtrationfiltering

Vorschrift

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.

Quelle