Floxuridine → Uridine, 2′-deoxy-5-fluoro-3′-O-[(4-fluorophenyl)methyl]-

HRID 466096

Reaction equation

HRID 466096 reaction equation
[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.[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>O.O1CCOCC1>[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]([O:12][CH2:25][C:24]2[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=2)[CH2:10]1

Participants

6

Reactant 3

HCID 5790FloxuridineHCID 96024-Fluorobenzyl chlorideHCID 14797Potassium Hydroxide

Product 1

HCID 10522044Uridine, 2′-deoxy-5-fluoro-3′-O-[(4-fluorophenyl)methyl]-Yield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
35 °C

Procedure

A 7.5 g quantity of potassium hydroxide was dissolved in a mixture of 300 ml of water and 80 ml of dioxane. To the solution were added 2.00 g of 2'-deoxy-5-fluorouridine and 4.9 ml of 4-fluorobenzyl chloride, and the resulting mixture was stirred at 35° C. for 2 days. After the reaction, the same subsequent procedure as in Reference Examples 4 and 5 was carried out, and the residue was placed on a silica gel column and eluted with 2% methanol-chloroform, thereby producing 0.57 g of the title compound in a yield of 20%.

Workup

  1. customAfter the reaction
  2. washeluted with 2% methanol-chloroform

Sources & evidence

ORD record
ord-399ca51a59ab462093a9d262cd6eb3b2
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Linked notes

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