Floxuridine → 2'-Deoxy-5-fluoro-3'-(2-methylbenzyl)uridine

HRID 466086

Reaktionsgleichung

Reaktionsgleichung von HRID 466086
[OH-].[K+].[F:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]1.[CH3:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Br>O.C(#N)C>[F:3][C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14][OH:15])[C@@:11]([CH2:20][C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2[CH3:23])([OH:12])[CH2:10]1

Komponenten

6

Edukt 3

HCID 5790FloxuridineHCID 6992o-Xylyl bromideHCID 14797Potassium Hydroxide

Produkt 1

HCID 542224992'-Deoxy-5-fluoro-3'-(2-methylbenzyl)uridineAusbeute 20,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A 1.14 g quantity of potassium hydroxide was dissolved in a mixture of 33 ml of water and 16 ml of acetonitrile. To the solution were added 1.00 g of 2'-deoxy-5-fluorouridine and 1.50 g of 2-methylbenzyl bromide at room temperature with stirring. Then the same subsequent procedures as in Examples 4 and 5 were conducted, giving 0.29 g of the title compound in a yield of 20%.

Quellen und Nachweise

ORD-Eintrag
ord-9c3a716382d945cfa97befce52e22a42
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155113

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