Hydrogen Peroxide → Acyclovir

HRID 1588949Notes

Reaction equation

HRID 1588949 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[C:10]([NH:11][C:12](=S)[NH2:13])=[C:9]([C:15]([NH2:17])=[O:16])[N:8]=[CH:7]1.OO>[OH-].[Na+].[O-][W]([O-])(=O)=O.[Na+].[Na+]>[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:7]=[N:8][C:9]2[C:15](=[O:16])[NH:17][C:12]([NH2:13])=[N:11][C:10]1=2

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 14897149HCID 14897149, compound

Product 1

HCID 135398513AcyclovirYield 59%

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 14798Sodium HydroxideSolvent

Procedure

1-[(2-Hydroxyethoxy)methyl]-5-(thiocarbamoyl)amino-1H-imidazole-4-carboxamide (2.59 g, 10.0 mM) and sodium tungstate (0.05 g) were dissolved in 6N sodium hydroxide (20 ml) at 5° C. 35% hydrogen peroxide (4.0 ml, 44 mM) was added dropwise at 5°-15° C. in the course of 15 minutes. After stirring for 15 minutes at 0°-5° C. HPLC indicated 59% yield of the title compound. The pH-value of the reaction mixture was adjusted to 5.5 with 25% aqueous acetic acid. The resulting product was filtered off, washed with water and dried which gave 1.13 g (50%) of the title compound as a white powder. HPLC indicated a purity of about 97%. The product had the same physical data as the product of example 5.

Sources & evidence

ORD record
ord-715bff38ee1f4dd5890a160485d11d71
Source dataset
uspto-grants-1993_06
Patent number
US05223619

Reaction notes

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