1,2,3,5-Tetraacetyl-beta-D-ribofuranose → 1-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carbonitrile

HRID 1703732Notes

Reaction equation

HRID 1703732 reaction equation
[C:1]([C:3]1[N:7]=[CH:6][NH:5][N:4]=1)#[N:2].C(O[C@@H:12]1[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]1[O:14][C:15](=[O:17])[CH3:16])(=O)C.P([O-])(OC1C=CC([N+]([O-])=O)=CC=1)(OC1C=CC([N+]([O-])=O)=CC=1)=O>C(Cl)(Cl)Cl>[C:1]([C:3]1[N:7]=[CH:6][N:5]([C@@H:12]2[O:24][C@H:23]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:13]2[O:14][C:15](=[O:17])[CH3:16])[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 5255575Bis(p-nitrophenyl)-phosphateHCID 178510603HCID 178510603, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3-cyano-1,2,4-triazole (9.41 g., 0.10 mol) and 1,2,3,5-tetra-O-acetyl-β -D-ribofuranose (31.8 g., 0.10 mol) was heated in an oil bath maintained at 150°. Bis(p-nitrophenyl) phosphate (100 mg.) was added with stirring and heating at 150° under diminished pressure was continued for 15 min. The residue was dissolved in chloroform, the solution was filtered and the solvent was removed. Crystallization of the residue from ether provided 28.2 g. (80%) of product with M.P. 96-97°.

Workup

  1. temperaturewas heated in an oil bath
  2. temperaturemaintained at 150°
  3. temperatureheating at 150° under diminished pressure
  4. filtrationthe solution was filtered
  5. customthe solvent was removed
  6. customCrystallization of the residue from ether
  7. customprovided 28.2 g

Sources & evidence

ORD record
ord-083541fcf06a4ad68edddddb140643e1
Source dataset
uspto-grants-1978_11
Patent number
USRE029835

Reaction notes

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