4-Methylbenzoyl Chloride → 2',3'-Dideoxy-3'-fluoro-5'-O-p-toluoyluridine
Reaktionsgleichung
[F:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=2)=[O:24])[O:5][C@@H:4]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a stirred solution of 2',3'-dideoxy-3'-fluorouridine (1 g, 4.34 mmoles) in dry pyridine (25 ml) at 0° C. was slowly added freshly distilled p-toluoyl chloride (0.63 ml, 4.78 mmoles). After the addition was complete, the mixture was stirred at 50° C. for 1.5 hrs., cooled and the solvent removed under reduced pressure. The residue was dissolved in chloroform (35 ml) and the solution extracted with 1M sulphuric acid (2×20 ml), water (2×30 ml) and dried (sodium sulphate). Evaporation of the solvent and purification of the residue by silica column chromatography eluting with 5% MeOH/CH2Cl2 afforded the title compound.
Aufarbeitung
- additionAfter the addition
- temperature, cooled
- customthe solvent removed under reduced pressure
- dissolutionThe residue was dissolved in chloroform (35 ml)
- extractionthe solution extracted with 1M sulphuric acid (2×20 ml), water (2×30 ml)
- dry with materialdried (sodium sulphate)
- customEvaporation of the solvent and purification of the residue by silica column chromatography
- washeluting with 5% MeOH/CH2Cl2
Quellen und Nachweise
- ORD-Eintrag
- ord-bcbd2a519bfb4ddc87d97494e1eac672
- Quelldatensatz
- uspto-grants-1992_10
- Patentnummer
- US05157114
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