Water → Acyclovir

HRID 865787Notes

Reaction equation

HRID 865787 reaction equation
C[Si](C)(C)[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:15]=[N:14][C:13]2[C:12](=[O:16])[NH:11][C:10]([NH2:17])=[N:9][C:8]1=2.O.O.[O-2].[O-2].[O-2].[O:25]=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>C(O)(=O)C>[OH:25][CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:15]=[N:14][C:13]2[C:12](=[O:16])[NH:11][C:10]([NH2:17])=[N:9][C:8]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 71586775BentoniteHCID 135976159HCID 135976159, compound

Product 1

HCID 135398513AcyclovirYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 9-(2-trimethylsilylethoxymethyl)guanine (15.8 g), water (250 ml), and acetic acid (20 ml) was heated to reflux, giving a solution. The hot solution was treated with a small amount of Montmorillonite K10 (an acidic clay) to remove any color, filtered, and the filtrate slowly cooled to 5° C. The white crystalline solid thus produced was filtered off, to yield 9-(2-hydroxyethoxymethyl)guanine (8.8 g, 69%). 1H NMR 3.38 (4H, singlet); 4.64 (1H, broad singlet); 5.26 (2H, singlet); 6.54 (2H, broad singlet); 7.68 (1H, singlet).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customgiving a solution
  4. customto remove any color
  5. filtrationfiltered
  6. customThe white crystalline solid thus produced
  7. filtrationwas filtered off

Sources & evidence

ORD record
ord-92ff83a8c4f5434b8739d3230828a8eb
Source dataset
uspto-grants-1996_10
Patent number
US05567816

Reaction notes

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