Ammonia → Ribavirin

HRID 1390340Notes

Reaction equation

HRID 1390340 reaction equation
C([C:3]([NH:5][NH2:6])=[NH:4])#N.CC1(C)[O:15][CH:14]2[CH:10]([CH:11]([CH2:17][OH:18])[O:12][CH:13]2O)[O:9]1.[CH2:20]([O:22]C(OCC)OCC)[CH3:21].[NH3:30]>>[C@@H:13]1([N:5]2[CH:3]=[N:4][C:21]([C:20]([NH2:30])=[O:22])=[N:6]2)[O:12][C@H:11]([CH2:17][OH:18])[C@@H:10]([OH:9])[C@H:14]1[OH:15]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 31214Ethyl orthoformateHCID 5477772,3-o-Isopropylidene-l-ribofuranoseHCID 178511376HCID 178511376, compound

Product 1

HCID 37542Ribavirin

Procedure

In a preferred method of synthesis as shown in Scheme I, cyanoformimidic acid hydrazide is reacted with 2,3-O-isopropylidene-D-ribose to yield N1 -(2,3-O-isopropylidene-D-ribofuranosyl)cyanoformamidrazone which is ring closed with triethylorthoformate followed by treatment with ammonia and acid hydrolysis of the isopropylidene group to yield 1-β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide. ##STR1##

Workup

  1. customIn a preferred method of synthesis
  2. customto yield N1 -(2,3-O-isopropylidene-D-ribofuranosyl)cyanoformamidrazone which

Sources & evidence

ORD record
ord-2896856f891740ada14e97c2e8f005ea
Source dataset
uspto-grants-1979_02
Patent number
US04138547

Reaction notes

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