Dicyclohexylcarbodiimide → Naproxen Succinimide

HRID 32336

Reaktionsgleichung

Reaktionsgleichung von HRID 32336
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[CH:12]=1.O[N:19]1[C:23](=[O:24])[CH2:22][CH2:21][C:20]1=[O:25].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[CH:12]=1.[C:20]1(=[O:25])[NH:19][C:23](=[O:24])[CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 156391Naproxen

Produkt 1

HCID 131727063Naproxen Succinimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

To Naproxen (2.303 g, 10 mmol) in 5 mL of dioxane was added N-hydroxysuccinimide (1.16 g, 10 mmol) dissolved in 15 mL of dioxane and dicyclohexylcarbodiimide (2.27 g, 11 mmol) in 25 mL of 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 30-40 mL CH2Cl2. Approximately 10 mL hexane was added and the mixture was chilled to 4° C. for 2 hr. Additional hexane was added dropwise until small planar white crystals began to form and the solution was refrigerated overnight. The activated ester was harvested, washed with hexane and dried in vacuum (2.30 g, 70.0%)

Aufarbeitung

  1. customthe insoluble dicyclohexylurea removed by filtration
  2. customThe solvent was removed by rotary evaporation
  3. dissolutionthe residue dissolved in 30-40 mL CH2Cl2
  4. additionApproximately 10 mL hexane was added
  5. additionAdditional hexane was added dropwise until small planar white crystals
  6. customto form
  7. waitthe solution was refrigerated overnight
  8. washwashed with hexane
  9. customdried in vacuum (2.30 g, 70.0%)

Quellen und Nachweise

ORD-Eintrag
ord-cc2db437f6ba4274b59e4b03fd5aa038
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427600B2

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