Chloroform → Acyclovir

HRID 614933Notes

Reaction equation

HRID 614933 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].C(Cl)(Cl)Cl>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

7

Reactant 3

HCID 6212ChloroformHCID 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 (0.22g) in water (30ml) was added a suspension of adenosine deaminase in aqueous ammonium sulfate (0.44ml, containing 4.4mg 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./0.1mm Hg for 16 hours to give 0.20g 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 4.4mg 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./0.1mm Hg for 16 hours

Sources & evidence

ORD record
ord-4abaa78fe43e4efb9bdbb320c9af115f
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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