Ammonia → HCID 21821194, compound

HRID 917827Notes

Reaction equation

HRID 917827 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1C1N=NNC=1)(=O)C.N.OO.[C@@H]1([N:36]2[N:40]=[C:39]([C:41]([NH2:43])=[O:42])[CH:38]=[N:37]2)O[C@H](CO)[C@@H](O)[C@H]1O>CC(O)C>[C@@H:6]1([N:37]2[CH:38]=[C:39]([C:41]([NH2:43])=[O:42])[N:40]=[N:36]2)[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 784Hydrogen Peroxide2×HCID 21825595HCID 21825595, compoundHCID 178476346HCID 178476346, compound

Product 1

HCID 21821194HCID 21821194, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Cyano-1-(2,3,5-tri-O-acetyl-β -D-ribofuranosyl-1,2,3-triazole (8). (0.35 g, 0.001 mol) was added to 15% aqueous ammonia (30 ml) and 30% hydrogen peroxide (3 ml). The solution was stirred 4 hr before additional hydrogen peroxide was added. The procedure and product isolation was identical to that used in method 2 for compound 4. The compound was dissolved in hot 2-propanol; cooling of the solution and filtering provided 30 mg of crystalline 5 which was identical to an authentic sample prepared by the procedure of Alonso, et al. J. Heterocyclic Chem. 7, 1269 (1970).

Workup

  1. additionwas added
  2. temperaturecooling of the solution
  3. filtrationfiltering
  4. customprovided 30 mg of crystalline 5 which
  5. customprepared by the procedure of Alonso, et al. J

Sources & evidence

ORD record
ord-2f2f15dc1b8c4d52abc9dbf26dd4d305
Source dataset
uspto-grants-1976_07
Patent number
US03968103

Reaction notes

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