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

HRID 466094Notes

Reaction equation

HRID 466094 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:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Cl>O.O1CCOCC1>[Cl:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][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 12103m,alpha-DichlorotolueneHCID 14797Potassium Hydroxide

Product 1

HCID 137150933'-O-(3-chlorobenzyl)-2'-deoxy-5-fluorouridineYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

A 2.00 g quantity of potassium hydroxide was dissolved in a mixture of 75 ml of water and 40 ml of dioxane. To the solution were added 1.00 g of 2'-deoxy-5-fluorouridine and 2.50 g of 3-chlorobenzyl chloride, and the resulting mixture was stirred at 45° C. for 3 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 to conduct a gradient elution with chloroform and mixtures of methanol (up to 2%) and chloroform, thereby producing 0.21 g of the title compound in a yield of 14%.

Workup

  1. customAfter the reaction
  2. washa gradient elution with chloroform and mixtures of methanol (up to 2%) and chloroform

Sources & evidence

ORD record
ord-1eb68a7537fe4740b9226099d92ebbd9
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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