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

HRID 466104

Reaktionsgleichung

Reaktionsgleichung von HRID 466104
[C:1]([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:34]=[C:33]([F:35])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24][C@@H:23]1[OH:36])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(Br)C1C=CC=CC=1.[OH-].[K+]>O1CCOCC1>[CH2:1]([O:20][C@@H:21]1[C@@H:22]([CH2:23][OH:36])[O:26][C@@H:25]([N:27]2[CH:34]=[C:33]([F:35])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

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

Produkt 1

HCID 10664574Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-Ausbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

In 50 ml of dioxane was dissolved 10 g of 2'-deoxy-5'-O-trityl-5-fluorouridine. To the solution were added 2.9 ml of benzyl bromide and 14.6 g of particles of potassium hydroxide. The mixture was stirred at room temperature for 1 hour. The solvent was distilled off and the residue was dissolved in 80 ml of a 80% solution of acetic acid to undergo reaction at 50° to 60° C. for 2 hours. The reaction mixture was cooled with ice for 1 hour, the trityl alcohol was separated by filtration and the mother liquor was concentrated. To the concentrate was added ethanol and the mixture was stirred. The crystals precipitated were separated by filtration and dried, affording 5.0 g of the title compound in a yield of 72%.

Aufarbeitung

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in 80 ml of a 80% solution of acetic acid
  3. customreaction at 50° to 60° C. for 2 hours
  4. temperatureThe reaction mixture was cooled with ice for 1 hour
  5. customthe trityl alcohol was separated by filtration
  6. concentrationthe mother liquor was concentrated
  7. additionTo the concentrate was added ethanol
  8. stirringthe mixture was stirred
  9. customThe crystals precipitated
  10. customwere separated by filtration
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-70939b8e63cd4aa28cc987d78df48095
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155113

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