Ethanol → 6-Deoxypenciclovir

HRID 1819714Notes

Reaction equation

HRID 1819714 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])=[C:4](Cl)[N:3]=1.C(OCC)(=O)C.C(O)C.[H][H]>[Pd].C(N(CC)CC)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 114257382-[2-(2-amino-6-chloro-9H-purine-9-yl)-ethyl]-1,3-propanediolHCID 178418361HCID 178418361, compound

Product 1

HCID 1285176-DeoxypenciclovirYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

The diol 4 (25 g, 9.2 mmol) was dissolved with a mixed solvent of ethyl acetate (200 ml) and ethanol (100 ml) in a 1 L steel autoclave. The palladium charcoal (5 g) and triethylamine (12 g) were added as well. The reaction mixture was kept at 55° C. under hydrogen pressure (0.8 Mpa) for 4 hours. The reaction was regarded as completed when no hydrogen intake was observed. The catalyst was removed by filtration after cooling down. The filtrate was concentrated by distillation under reduced pressure. The residue was dissolved by addition of DCM and water. The separated aqueous layer was extracted with more DCM (30 ml×3). The combined organic solution was dried and distilled to remove solvent. The residue was dissolved with ethyl acetate (80 ml) and kept at room temperature for 4 hours. The product was collected by filtration and dried under vacuum (18 g, yield 82%).

Workup

  1. customwas kept at 55° C. under hydrogen
  2. customfor 4 hours
  3. customThe catalyst was removed by filtration
  4. temperatureafter cooling down
  5. concentrationThe filtrate was concentrated by distillation under reduced pressure
  6. dissolutionThe residue was dissolved by addition of DCM and water
  7. extractionThe separated aqueous layer was extracted with more DCM (30 ml×3)
  8. customThe combined organic solution was dried
  9. distillationdistilled
  10. customto remove solvent
  11. dissolutionThe residue was dissolved with ethyl acetate (80 ml)
  12. filtrationThe product was collected by filtration
  13. customdried under vacuum (18 g, yield 82%)

Sources & evidence

ORD record
ord-e18ff108db6a4368acc0a13fbfb10de2
Source dataset
uspto-grants-2009_10
Patent number
US07601835B2

Reaction notes

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