Formic Acid → Penciclovir

HRID 2291842Notes

Reaction equation

HRID 2291842 reaction equation
C([O:8][CH2:9][CH:10]([CH2:24][O:25]CC1C=CC=CC=1)[CH2:11][CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([NH2:23])=[N:17][C:18]=2Cl)C1C=CC=CC=1.C(O)=[O:34]>[Pd]>[OH:8][CH2:9][CH:10]([CH2:24][OH:25])[CH2:11][CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:34])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2

Participants

4

Reactant 2

HCID 284Formic AcidHCID 14605506HCID 14605506, compound

Product 1

HCID 135398748PenciclovirYield 45%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 4-(2-amino-6-chloropurin-9-yl)-2-benzyloxymethylbutyl benzyl ether (0.904 g, 2 mmol) in 25 ml of 80% aqueous formic acid was kept at 100° C. for 1h, palladium catalyst (10% on carbon, 0.40 g) was added, and the mixture was hydrogenated at room temperature and atmospheric pressure with efficient stirring for 45 min. After evaporation in vacuum to dryness the residue was heated to boiling with 50 ml of water, 1 ml of concentrated aqueous ammonia was added, the solution was boiled gently for a short while and then evaporated to dryness. Recrystallization from water afforded 0.23 g (45%) of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine. M.p. 252°-262° C. (decomposition, slow heating) or 264°-265° (fast immersion of the capillary).

Workup

  1. additionwas added
  2. customwas hydrogenated at room temperature
  3. customAfter evaporation in vacuum to dryness the residue
  4. temperaturewas heated
  5. additionwas added
  6. customevaporated to dryness
  7. customRecrystallization from water

Sources & evidence

ORD record
ord-4f5c4114d15d44848388b7454800259c
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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