Sodium Iodide → 2'-deoxy-3'-O-benzyl-5'-O-trityl-5-fluorouridine

HRID 466103

Reaktionsgleichung

Reaktionsgleichung von HRID 466103
[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)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:37](Cl)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[OH-].[K+].[I-].[Na+]>O1CCOCC1.O.C(O)(=O)C>[CH2:37]([O:36][C@@H:23]1[C@@H:22]([CH2:21][O:20][C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[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:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 7503Benzyl Chloride2×HCID 14797Potassium Hydroxide3×HCID 108387042'-deoxy-5'-O-trityl-5-fluorouridine

Produkt 1

HCID 106747232'-deoxy-3'-O-benzyl-5'-O-trityl-5-fluorouridineAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A 10 g quantity of 2'-deoxy-5'-O-trityl-5-fluorouridine was dissolved in 100 ml of dioxane. To the solution were added 2.9 ml of benzyl chloride, 6.9 g of particles of potassium hydroxide and 3.56 g of sodium iodide. The mixture was stirred at 40° C. for 4 hours, and 2.9 ml of benzyl chloride and 1.15 g of potassium hydroxide were added and stirred for 1 hour. Thereto was added water to dissolve the potassium hydroxide in water. The solution was adjusted to a pH of about 3 with acetic acid and extracted with ethylene dichloride. The extract was washed with water and the ethylene dichloride layer was dried over anhydrous sodium sulfate. The sodium sulfate was separated by filtration and the solvent was distilled off, giving 8 g of 2'-deoxy-3'-O-benzyl-5'-O-trityl-5-fluorouridine as an oil.

Aufarbeitung

  1. stirringstirred for 1 hour
  2. extractionextracted with ethylene dichloride
  3. washThe extract was washed with water
  4. dry with materialthe ethylene dichloride layer was dried over anhydrous sodium sulfate
  5. customThe sodium sulfate was separated by filtration
  6. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-a32d777dd9ca42ef9ca0c896fd643e53
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155113

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