Potassium Hydroxide → HCID 15124909, Verbindung

HRID 981733

Reaktionsgleichung

Reaktionsgleichung von HRID 981733
[F:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:35])[N:6]([CH:34]=1)[C@@H:7]1[O:33][C@H:11]([CH2:12][O:13]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:9]([OH:10])[CH2:8]1.[OH-].[K+].[Br:39][C:40]1[S:41][C:42]([CH2:47]Cl)=[C:43]([Br:46])[C:44]=1[Br:45]>O1CCOCC1>[F:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:35])[N:6]([CH:34]=1)[C@@H:7]1[O:33][C@H:11]([CH2:12][OH:13])[C@@H:9]([O:10][CH2:47][C:42]2[S:41][C:40]([Br:39])=[C:44]([Br:45])[C:43]=2[Br:46])[CH2:8]1

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 108387042'-deoxy-5'-O-trityl-5-fluorouridineHCID 151249082,3,4-Tribromo-5-(chloromethyl)thiophene

Produkt 1

HCID 15124909HCID 15124909, VerbindungAusbeute 18,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5.00 g of 2'-deoxy-5-fluoro-5'-O-trityluridine in 100 ml of dioxane were added 5.74 g of fine powder of potassium hydroxide and 5.65 g of 2,3,4- tribromo-5-chloromethylthiophene, and the mixture was stirred at a temperature of 80° C. for 2 hours. The reaction mixture was concentrated and the residue was dissolved in 100 ml of ethyl acetate. The solution was washed with aqueous solution of acetic acid, dried and concentrated. To the residue was added 100 ml of 80% acetic acid and the mixture was left to stand at a temperature of 80° C. for one hour. The solvent was distilled off and the residue was placed on silica gel column and eluted with 2% methanol-chloroform for purification, giving 1.07 g (18%) of the desired 2'-deoxy 5-fluoro-3'-O-(3,4,5-tribromo-2-thenyl)uridine.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in 100 ml of ethyl acetate
  3. washThe solution was washed with aqueous solution of acetic acid
  4. customdried
  5. concentrationconcentrated
  6. additionTo the residue was added 100 ml of 80% acetic acid
  7. waitthe mixture was left
  8. waitto stand at a temperature of 80° C. for one hour
  9. distillationThe solvent was distilled off
  10. washeluted with 2% methanol-chloroform for purification

Quellen und Nachweise

ORD-Eintrag
ord-b804364ba17d4ef4a3b26b125af93c3a
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04992534

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