Ammonium formate → 6-Deoxypenciclovir

HRID 5867

Reaction equation

HRID 5867 reaction equation
C([O:4][CH2:5][CH:6]([CH2:20][O:21]C(=O)C)[CH2:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][C:12]([NH2:19])=[N:13][C:14]=2Cl)(=O)C.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:19][C:12]1[N:11]=[C:10]2[C:15]([N:16]=[CH:17][N:9]2[CH2:8][CH2:7][CH:6]([CH2:20][OH:21])[CH2:5][OH:4])=[CH:14][N:13]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 101551646-Chloro famciclovir

Product 1

HCID 1285176-Deoxypenciclovir

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine (4.86 g, 13.7 mmol) in methanol (140 ml) containing ammonium formate (400 mM) was added 10% palladium-on-charcoal (0.4 g) and the mixture was heated under reflux for 40 minutes. After cooling the solution was filtered and the solvent removed. The residue was taken up in water and extracted with chloroform (100 ml and 50 ml). The organic layers were combined, dried (magnesium sulphate) and the solvent removed. The residue was dissolved in methanol saturated with ammonia at 0° C. (150 ml) and the solution was stirred for 20 hours. The solvent was removed and the residue suspended in chloroform (20 ml) and filtered. The solid was recrystallised from isopropanol-water and a second recrystallisation was carried out from the mother liquors from ethanol (total 2.71 g, 83%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 40 minutes
  3. temperatureAfter cooling the solution
  4. filtrationwas filtered
  5. customthe solvent removed
  6. extractionextracted with chloroform (100 ml and 50 ml)
  7. dry with materialdried (magnesium sulphate)
  8. customthe solvent removed
  9. dissolutionThe residue was dissolved in methanol saturated with ammonia at 0° C. (150 ml)
  10. customThe solvent was removed
  11. filtrationfiltered
  12. customThe solid was recrystallised from isopropanol-water
  13. customa second recrystallisation

Sources & evidence

ORD record
ord-9a26110b23a143e0bf216102d09220cd
Source dataset
uspto-grants-1993_09
Patent number
US05246937

Linked notes

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