Uridine → Ribavirin

HRID 256511

Reaction equation

[NH:1]1[CH:5]=[N:4][C:3]([C:6]([NH2:8])=[O:7])=[N:2]1.N1C=CN=N1.[C@@H:14]1(N2C=CC(=O)NC2=O)[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]1[OH:16].[C@@H]1(N2C3N=CN=C(O)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.[C@@H]1(N2C=CC(N)=NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.[C@@H]1(N2C3N=C(N)NC(=O)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.P([O-])(O)(O)=O.[K+]>>[CH:5]1[N:1]([C@@H:14]2[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]2[OH:16])[N:2]=[C:3]([C:6]([NH2:8])=[O:7])[N:4]=1

Participants

Reactant 8

HCID 6029Uridine

HCID 6175Cytidine

HCID 60961Adenosine

HCID 516951Monobasic potassium phosphate

HCID 135398635Guanosine

HCID 178418936HCID 178418936, compound

HCID 178513825HCID 178513825, compound

HCID 178521066(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol

Product 1

HCID 37542Ribavirin

Procedure

By using a substrate solution (pH 6.0) containing 40 mM 1, 2, 4-triazole-3-carboxamide (hereinafter called "triazole") as the base donor, 40 mM uridine, inosine, cytidine, adenosine or guanosine as the saccharide residue donor and 40 mM potassium dihydrogenphosphate, ribavirin was produced in the same manner as in Example 1. The results are shown in Table 7.

Sources & evidence

ORD record: ord-083540e260744b8b94717887f3bd53ce
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258301

Linked notes

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