Triethylamine → HCID 12802104, compound

HRID 2164224Notes

Reaction equation

HRID 2164224 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][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37]>O1CCOCC1>[CH3:33][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36]([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:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 12802102HCID 12802102, compound

Product 1

HCID 12802104HCID 12802104, compoundYield 56.4%

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 1.7 g of 2-methylbenzoyl chloride are added to the solution and the mixture is subjected to reaction at room temperature for 15 minutes and then at 70° C. for 30 minutes. The reaction liquid is cooled and triethylamine hydrochloride is filtered off. The filtrate is concentrated under reduced pressure and the oily residue is purified by column chromatography on silica gel (elution solvent: chloroform). The The purified oily substance is dissolved in about 15 ml of dimethyl sulfoxide and the solution is added dropwise to about 400 ml of ice water under vigorous agitation whereupon a precipitate is formed. The resultant precipitate is collected by filtration, washed with water and dried at room temperature under reduced pressure whereby 1.5 g (yield: 56.4%) of powdery 3-(2-methylbenzoyl)-2'-deoxy-3',5'-di-O-propionyl-5-fluorouridine are obtained.

Workup

  1. temperaturecooled
  2. customthe mixture is subjected to reaction at room temperature for 15 minutes
  3. customThe reaction liquid
  4. temperatureis cooled
  5. filtrationtriethylamine hydrochloride is filtered off
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customthe oily residue is purified by column chromatography on silica gel (elution solvent: chloroform)
  8. dissolutionThe The purified oily substance is dissolved in about 15 ml of dimethyl sulfoxide
  9. additionthe solution is added dropwise to about 400 ml of ice water under vigorous agitation whereupon a precipitate
  10. customis formed
  11. filtrationThe resultant precipitate is collected by filtration
  12. washwashed with water

Sources & evidence

ORD record
ord-b3ca7af4aeb34ceeb1c100fc33d5932b
Source dataset
uspto-grants-1985_03
Patent number
US04503045

Reaction notes

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