Water → HCID 178508925, compound

HRID 899487Notes

Reaction equation

HRID 899487 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.[OH2:25].[OH-].[Na+]>C(O)=O>[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.[CH:17]1[N:9]([CH2:8][CH2:7][CH:6]([CH2:20][OH:21])[CH2:5][OH:4])[C:10]2[N:11]=[C:12]([NH2:19])[N:13]=[C:14]([OH:25])[C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 101551646-Chloro famciclovir

Product 1

HCID 178508925HCID 178508925, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Conditions

Temperature
42.5 °C

Procedure

A mixture of 9-(4-acetoxy-3-acetoxymethylbut-l-yl)-2-amino-6-chloropurine (10 g, 28.1 mmole), formic acid (96%, 6.3 ml) and water (55 ml) was stirred and heated to reflux for about 4 hours. After cooling the solution was basified by mixing with sodium hydroxide solution (12.5M, 27 ml) and the resulting solution was stirred for 1.5 hrs. The solution was neutralised by the addition of formic acid. The resultant slurry was heated to reflux (ca 105° C.) then cooled to 40-45° C. and stirred for about 3 hours. The crude product is then isolated and washed with water (20 ml). The isolated product was dissolved in sodium hydroxide solution (3M, 80 ml). Carbon (ca 1.5 g) was added and the slurry stirred for about 1 hr then the carbon was removed by filtration and washed with water (20 ml). The solution was neutralised by the addition of formic acid and the resultant precipitate was redissolved by heating to ca 100° C. and was then cooled. The precipitated product was stirred for about 3 hrs then isolated and washed with water (2×20 ml) before being dried.

Workup

  1. temperatureheated
  2. temperatureto reflux for about 4 hours
  3. temperatureAfter cooling the solution
  4. stirringthe resulting solution was stirred for 1.5 hrs
  5. temperatureThe resultant slurry was heated
  6. temperatureto reflux (ca 105° C.)
  7. stirringstirred for about 3 hours

Sources & evidence

ORD record
ord-3fa59a9b25ef421ea4aa9ad0887bf824
Source dataset
uspto-grants-2008_04
Patent number
US07355043B2

Reaction notes

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