Gemfibrozil → Gemfibrozil Succinimide

HRID 32337

Reaktionsgleichung

Reaktionsgleichung von HRID 32337
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([O:8][CH2:9][CH2:10][CH2:11][C:12]([C:15]([OH:17])=[O:16])([CH3:14])[CH3:13])[CH:7]=1.O[N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([O:8][CH2:9][CH2:10][CH2:11][C:12]([C:15]([OH:17])=[O:16])([CH3:13])[CH3:14])[CH:7]=1.[C:21]1(=[O:26])[NH:20][C:24](=[O:25])[CH2:23][CH2:22]1

Komponenten

5

Edukt 3

HCID 3463GemfibrozilHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Produkt 1

HCID 86585518Gemfibrozil Succinimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

To Gemfibrozil (GEM) (5.0 g, 20.0 mmol) in 30 mL dioxane was added N-hydroxysuccinimide (2.3 g, 20.0 mmol) in 20 mL dioxane and dicyclohexylcarbodiimide (4.5 g, 22.0 mmol) in 50 mL dioxane. The reaction was stirred overnight and the insoluble dicyclohexylurea removed by filtration. The solvent was removed by rotary evaporation and the residue dissolved in 15-20 mL of CH2Cl2. Hexane was added dropwise until crystal formation was seen and the mixture was chilled to 4° C. overnight. Approximately 3 mL of additional n-hexane was added and the mixture chilled to −20° C. overnight. The activated ester formed small planer crystals and was harvested, washed with hexane and dried in vacuum (5.8 g, 80%).

Aufarbeitung

  1. customthe insoluble dicyclohexylurea removed by filtration
  2. customThe solvent was removed by rotary evaporation
  3. dissolutionthe residue dissolved in 15-20 mL of CH2Cl2
  4. additionHexane was added dropwise until crystal formation
  5. additionApproximately 3 mL of additional n-hexane was added
  6. temperaturethe mixture chilled to −20° C. overnight
  7. washwashed with hexane
  8. customdried in vacuum (5.8 g, 80%)

Quellen und Nachweise

ORD-Eintrag
ord-83f6f1e171f2410d9012f6843e85c92c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427600B2

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