Acetic Anhydride → O-Acetyldeoxyacyclovir

HRID 64627Notes

Reaction equation

HRID 64627 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][C:9]([NH2:15])=[N:10][CH:11]=2.[C:16](OC(=O)C)(=[O:18])[CH3:17]>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:16]([O:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][C:9]([NH2:15])=[N:10][CH:11]=2)(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 552562-[(2-Amino-9H-purin-9-yl)methoxy]ethan-1-ol

Product 1

HCID 10422259O-Acetyldeoxyacyclovir

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.82 g (3.92 mM) of 9-(2-hydroxyethoxymethyl)-2-amino-9H-purine, 48 mg (0.392 mM) of a 4-dimethylaminopyridine and 0.75 ml (7.84 mM) of acetic anhydride in 18 ml of dry dimethylformamide was stirred at room temperature for two days. The reaction mixture was evaporated in vacuo and the residue dissolved in ethyl acetate and absorbed on silica gel. The solvent was removed by flash evaporation and the residual powder added to a column prepared for flash chromatography. Elution with 5% methanol in dichloromethane gave 1.0 g of a semicrystalline oil which on recrystallization from benzene-hexane gave analytically pure 9-(2-acetoxyethoxymethyl)-2-amino-9H-purine, mpt. 115°-118° C. An additional crop was obtained from the mother liquor.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. customabsorbed on silica gel
  4. customThe solvent was removed by flash evaporation
  5. additionthe residual powder added to a column
  6. customprepared for flash chromatography
  7. washElution with 5% methanol in dichloromethane
  8. customgave 1.0 g of a semicrystalline oil which
  9. customon recrystallization from benzene-hexane

Sources & evidence

ORD record
ord-36d240ac62694166b65b0e5066e56183
Source dataset
uspto-grants-1986_09
Patent number
US04609662

Reaction notes

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