5-Fluorouridine → Doxifluridine

HRID 1719780

Reaktionsgleichung

Reaktionsgleichung von HRID 1719780
[F:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13]O)[C@@H:10]([OH:11])[C@H:8]1[OH:9]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH3:13])[C@@H:10]([OH:11])[C@H:8]1[OH:9]

Komponenten

3

Edukt 1

HCID 94275-Fluorouridine

Produkt 1

HCID 18343DoxifluridineAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

The 5-Fluorouridine derivative obtained in Example 4 (1.77 g, 6.18 mmol) was dissolved in a 90% by weight aqueous solution of CF3COOH (10 ml) and reacted at a room temperature for 1 hour with stirring. After the reaction, the reaction mixture was evaporated under a reduced pressure. The residue was recrystallized from methanol to obtain white crystalline 5'-deoxy-5-fluorouridine (1.40 g, 5.69 mmol. Yield, 92.1%) of the formula: ##STR14##

Aufarbeitung

  1. customreacted at a room temperature for 1 hour
  2. customAfter the reaction
  3. customthe reaction mixture was evaporated under a reduced pressure
  4. customThe residue was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-12d1e675f3b64accadd7ecd4061c1b4d
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04542209

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