Ammonia → 1-(5-O-Benzoyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide

HRID 1287207Notes

Reaction equation

HRID 1287207 reaction equation
C[O:2][C:3]([C:5]1[N:9]=[CH:8][N:7]([C@@H:10]2[O:32][C@H:31]([CH2:33][O:34][C:35](=[O:42])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@@H:21]([O:22]C(=O)C3C=CC=CC=3)[C@H:11]2[O:12]C(=O)C2C=CC=CC=2)[N:6]=1)=O.[NH3:43]>CO>[C:35]([O:34][CH2:33][C@H:31]1[O:32][C@@H:10]([N:7]2[CH:8]=[N:9][C:5]([C:3]([NH2:43])=[O:2])=[N:6]2)[C@H:11]([OH:12])[C@@H:21]1[OH:22])(=[O:42])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 134568041-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester

Product 1

HCID 227929641-(5-O-Benzoyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester and methanol saturated at 0° with anhydrous ammonia was stirred at 0° for 4 hr. The resulting solution was evaporated to dryness under reduced pressure and the product was crystallized from aqueous ethanol to give 1-(5-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide with mp 182°-184°.

Workup

  1. customThe resulting solution was evaporated to dryness under reduced pressure
  2. customthe product was crystallized from aqueous ethanol

Sources & evidence

ORD record
ord-9b9081c3a14b4ab9a2e98bc88ee67ca7
Source dataset
uspto-grants-1976_10
Patent number
US03984396

Reaction notes

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