Sodium Hydroxide → Penciclovir

HRID 1368680Notes

Reaction equation

HRID 1368680 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.[OH-:25].[Na+]>Cl>[OH:4][CH2:5][CH:6]([CH2:20][OH:21])[CH2:7][CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:14](=[O:25])[NH:13][C:12]([NH2:19])=[N:11][C:10]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 101551646-Chloro famciclovir

Product 1

HCID 135398748PenciclovirYield 85%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 9-(4-acetoxy-3-acetoxymethyl-but-1-yl)-2-amino-6-chloropurine (15.5 g, 43.6 mmol) in 2M hydrochloric acid (150 ml) was heated under reflux for 2 hours. The solution was then cooled to room temperature and neutralised with 10% sodium hydroxide solution, left to stand at 4° C., and the resulting precipitate filtered off, washed with cold water and recrystallized from water to give 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine as a white crystalline solid (9.4 g, 85%) mp 275-277°.

Workup

  1. temperatureunder reflux for 2 hours
  2. waitleft
  3. customto stand at 4° C.
  4. filtrationthe resulting precipitate filtered off
  5. washwashed with cold water
  6. customrecrystallized from water

Sources & evidence

ORD record
ord-920a8c813cd64dd6a8b7b06d0379ecfe
Source dataset
uspto-grants-2003_06
Patent number
US06573378B1

Reaction notes

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