Triethylamine → HCID 13394185, compound

HRID 2164226Notes

Reaction equation

HRID 2164226 reaction equation
[C:1]([O:5][C@@H:6]1[C@@H:10]([CH2:11][O:12][C:13](=[O:16])[CH2:14][CH3:15])[O:9][C@@H:8]([N:17]2[CH:24]=[C:23]([F:25])[C:21](=[O:22])[NH:20][C:18]2=[O:19])[CH2:7]1)(=[O:4])[CH2:2][CH3:3].C(N(CC)CC)C.[CH3:33][O:34][C:35]1[C:43]([O:44][CH3:45])=[CH:42][CH:41]=[CH:40][C:36]=1[C:37](Cl)=[O:38]>O1CCOCC1>[CH3:33][O:34][C:35]1[C:43]([O:44][CH3:45])=[CH:42][CH:41]=[CH:40][C:36]=1[C:37]([N:20]1[C:21](=[O:22])[C:23]([F:25])=[CH:24][N:17]([C@@H:8]2[O:9][C@H:10]([CH2:11][O:12][C:13](=[O:16])[CH2:14][CH3:15])[C@@H:6]([O:5][C:1](=[O:4])[CH2:2][CH3:3])[CH2:7]2)[C:18]1=[O:19])=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27583922,3-Dimethoxybenzoyl chlorideHCID 12802102HCID 12802102, compound

Product 1

HCID 13394185HCID 13394185, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.0 Grams of 2'-deoxy-3',5'-di-O-propionyl-5-fluorouridine are dissolved in 25 ml of dry dioxane and the solution is ice cooled. 2 Milliliters of triethylamine and 2.2 g of 2,3-dimethoxybenzoyl chloride are added to the solution and the mixture is subjected to reaction at room temperature for 30 minutes and then at 50° C. for 30 minutes. The reaction liquid is cooled and then triethylamine hydrochloride is filtered off. The filtrate is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel (elution solvent: chloroform). The purified oily substance is allowed to stand overnight at room temperature whereby a part of the substance is crystallized. A small amount of ethanol is added to crystallize the substance wholly and the crystals are collected by filtration whereby 2.3 g (yield: 79.0%) of 3-(2,3-dimethoxybenzoyl)-2'-deoxy-3',5'-di-O-propionyl-5-fluorouridine are obtained. M.P. 84.5°-86° C.

Workup

  1. temperaturecooled
  2. customthe mixture is subjected to reaction at room temperature for 30 minutes
  3. customThe reaction liquid
  4. temperatureis cooled
  5. filtrationtriethylamine hydrochloride is filtered off
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customthe residue is purified by column chromatography on silica gel (elution solvent: chloroform)
  8. waitto stand overnight at room temperature
  9. customwhereby a part of the substance is crystallized
  10. additionA small amount of ethanol is added
  11. customto crystallize the substance wholly

Sources & evidence

ORD record
ord-fa28742cc8334cca9db02c63710ea53a
Source dataset
uspto-grants-1985_03
Patent number
US04503045

Reaction notes

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