Desciclovir → O-Acetyldeoxyacyclovir

HRID 1252682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1252682
[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.[CH3:16][C:17](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:18]>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:17]([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])[CH3:16]

Komponenten

5

Edukt 2

HCID 55256DesciclovirHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Produkt 1

HCID 10422259O-Acetyldeoxyacyclovir

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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 anhyride 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e230f6b81633455cb4f47dbfbdc7db06
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04745119

Notizen zur Reaktion

Wird geladen…