Ammonia → HCID 11793496, compound

HRID 1944792Notes

Reaction equation

HRID 1944792 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@@H:6]1[N:19]1[CH:23]=[N:22][C:21]([C:24]([O:26]C)=O)=[N:20]1)(=[O:3])[CH3:2].[NH3:28]>CO>[C:1]([O:4][C@H:5]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[O:7][C@@H:6]1[N:19]1[CH:23]=[N:22][C:21]([C:24]([NH2:28])=[O:26])=[N:20]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10691464Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate

Product 1

HCID 11793496HCID 11793496, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1,2,4-triazole-3-carboxylate and 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose are heated under reduced pressure in the presence of trifluoromethanesulfonic acid or bis(p-nitrophenyl)-phosphate. The residue is recrystallized from ethanol or methanol to obtain methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate. Subsequently, the obtained methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate is treated with ammonia in a methanol solvent, and the resultant mixture is then recrystallized from ethanol to obtain a crude product of 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxamide. The obtained compound is further recrystallized from an ethanol aqueous solution, so as to obtain high-purity 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxamide.

Workup

  1. customthe resultant mixture is then recrystallized from ethanol

Sources & evidence

ORD record
ord-1f39e0ae41bb4cdb9042efcb5312cbe2
Source dataset
uspto-grants-2013_03
Patent number
US08394935B2

Reaction notes

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