Adenosine → Acyclovir

HRID 2050018Notes

Reaction equation

HRID 2050018 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][OH:15])=[C:4](N)[N:3]=1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:19]>O.S([O-])([O-])(=O)=O.[NH4+].[NH4+].CO>[OH:15][CH2:14][CH2:13][O:12][CH2:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:19])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

6

Reactant 2

HCID 60961AdenosineHCID 945882,6-Diamino-9-(2-hydroxyethoxymethyl)purine

Product 1

HCID 135398513Acyclovir

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6097028Ammonium SulfateSolvent

Procedure

To a solution of 2-amino-9-(2-hydroxyethoxymethyl)adenine (0.22 g) in water (30 ml) was added a suspension of adenosine deaminase in aqueous ammonium sulfate (0.44 ml, containing 4.4 mg of the enzyme). The reaction mixture, which initially had a pH of 7.0, was heated at 37° C. for 18 hours, at which time the pH was 8.5 and TLC (silica gel plates developed in 15% methanol-85% chloroform) indicated a single product different from starting material. The reaction mixture was thoroughly chilled in an ice bath and the resulting white solid removed by filtration and thoroughly washed with cold water. The product was dried at 100° C./0.1 mm Hg for 16 hours to give 0.20 g of 9-(2-hydroxyethoxymethyl)guanine. 1/4 H2O, the structure of which was confirmed by m.p., TLC, U.V., NMR and mass spectroscopy analysis. Recrystallization from methanol gave the anhydrous 9-(2-hydroxyethoxymethyl)guanine.

Workup

  1. additioncontaining 4.4 mg of the enzyme)
  2. temperatureThe reaction mixture was thoroughly chilled in an ice bath
  3. customthe resulting white solid removed by filtration
  4. washthoroughly washed with cold water
  5. customThe product was dried at 100° C./0.1 mm Hg for 16 hours

Sources & evidence

ORD record
ord-2fecbbdc4a44417786332280e0e7973d
Source dataset
uspto-grants-1980_04
Patent number
US04199574

Reaction notes

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