Reaktion #60614

Reaktionsgleichung

dicyclohexylcarbodiimide

Naproxen

N-hydroxysuccinimide

→

Naproxen Succinimide

Lösungsmittel

dioxane

dioxane

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe insoluble dicyclohexylurea removed by filtration
2. 2
   SonstigeThe solvent was removed by rotary evaporation
3. 3
   workup.DISSOLUTIONthe residue dissolved in 30-40 mL CH2Cl2
4. 4
   workup.ADDITIONApproximately 10 mL hexane was added
5. 5
   workup.ADDITIONAdditional hexane was added dropwise until small planar white crystals
6. 6
   Sonstigeto form
7. 7
   workup.WAITthe solution was refrigerated overnight
8. 8
   Waschenwashed with hexane
9. 9
   Sonstigedried in vacuum (2.30 g, 70.0%)

Vorschrift

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%)

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