Benzene → Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-

HRID 466085

Reaktionsgleichung

Reaktionsgleichung von HRID 466085
C1C=CC=CC=1.[F:7][C:8]1[C:9](=[O:42])[NH:10][C:11](=[O:41])[N:12]([CH:40]=1)[C@@H:13]1[O:39][C@H:17]([CH2:18][O:19]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:15]([OH:16])[CH2:14]1.[CH2:43](Br)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[OH-].[K+]>O1CCOCC1>[CH2:43]([O:16][C@@H:15]1[C@@H:17]([CH2:18][OH:19])[O:39][C@@H:13]([N:12]2[CH:40]=[C:8]([F:7])[C:9](=[O:42])[NH:10][C:11]2=[O:41])[CH2:14]1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 108387042'-deoxy-5'-O-trityl-5-fluorouridine

Produkt 1

HCID 10664574Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-Ausbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a mixture of 50 ml of benzene and 50 ml of dioxane were added 1.00 g of 2'-deoxy-5-fluoro-5'-O-trityluridine, 0.30 ml of benzyl bromide and 0.23 g of potassium hydroxide powder, and the mixture was refluxed for 25 hours. The insolubles were removed by filtration and the filtrate was concentrated and the concentrate was dissolved in 5 ml of 80% acetic acid. The solution was left to stand at 80° C. for 2 hours. The solvent was distilled off and the residue was placed on a silica gel column to conduct a gradient elution using chloroform and mixtures of methanol (up to 2%) and chloroform. The fractions corresponding to 3'-O-benzyl-2'-deoxy-5-fluorouridine were collected and concentrated. The concentrate was recrystallized from ethanol, giving 0.14 g of the title compound in a yield of 20%.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 25 hours
  2. customThe insolubles were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. dissolutionthe concentrate was dissolved in 5 ml of 80% acetic acid
  5. waitThe solution was left
  6. distillationThe solvent was distilled off
  7. washa gradient elution
  8. customThe fractions corresponding to 3'-O-benzyl-2'-deoxy-5-fluorouridine were collected
  9. concentrationconcentrated
  10. customThe concentrate was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-85b329a2a10f4a8388d5b30f839bd77c
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155113

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