Ammonia → Ribavirin

HRID 1703729Notes

Reaction equation

HRID 1703729 reaction equation
C[O:2][C:3]([C:5]1[N:9]=[CH:8][N:7]([C@@H:10]2[O:22][C@H:21]([CH2:23][O:24]C(=O)C)[C@@H:16]([O:17]C(=O)C)[C@H:11]2[O:12]C(=O)C)[N:6]=1)=O.[NH3:28]>CO>[C@@H:10]1([N:7]2[CH:8]=[N:9][C:5]([C:3]([NH2:28])=[O:2])=[N:6]2)[O:22][C@H:21]([CH2:23][OH:24])[C@@H:16]([OH:17])[C@H:11]1[OH:12]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10150551Methyl 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylate

Product 1

HCID 37542RibavirinYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(2,3,5-tri-O-acetyl-β -D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (10.0 g., 26.0 mmole) in methanol (70 ml.) saturated at 0° with anhydrous ammonia was kept in a sealed pressure flask at 25° for 18 hrs. The product was crystallized from ethanol to give 1-(β -D-ribofuranosyl)-1,2,4-triazole-3-carboxamide (5.70 g., 90.0%).

Workup

  1. customThe product was crystallized from ethanol

Sources & evidence

ORD record
ord-df85ffb2cfb44b359c7b99493654d008
Source dataset
uspto-grants-1978_11
Patent number
USRE029835

Reaction notes

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