Floxuridine → 3'-O-(2-chlorobenzyl)-2'-deoxy-5-fluorouridine

HRID 1607330

Reaction equation

HRID 1607330 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.[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Cl>O.O1CCOCC1>[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][O:12][C@@H:11]1[C@@H:13]([CH2:14][OH:15])[O:16][C@@H:9]([N:8]2[CH:17]=[C:4]([F:3])[C:5](=[O:19])[NH:6][C:7]2=[O:18])[CH2:10]1

Participants

6

Reactant 3

HCID 5790FloxuridineHCID 119062-Chlorobenzyl chlorideHCID 14797Potassium Hydroxide

Product 1

HCID 137150953'-O-(2-chlorobenzyl)-2'-deoxy-5-fluorouridineYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
30 °C

Procedure

A 3.75 g quantity of potassium hydroxide was dissolved in a mixture of 150 ml of water and 40 ml of dioxane. To the solution were added 1.00 g of 2'-deoxy-5-fluorouridine and 10 ml of 2-chlorobenzyl chloride, and the resulting mixture was stirred at 30° C. for 3 days. After the reaction, the same subsequent procedure as in 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 0.34 g of the title compound in a yield of 23%.

Workup

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

Sources & evidence

ORD record
ord-db5478d73a0d44d0b7a29eb328ec7ff7
Source dataset
uspto-grants-1989_09
Patent number
US04864021

Linked notes

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