Dicyclohexylcarbodiimide → Naproxen Succinimide

HRID 32336

Reaction equation

[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

Participants

Conditions

Temperature: 4 °C

Procedure

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%)

Workup

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

Sources & evidence

ORD record: ord-cc2db437f6ba4274b59e4b03fd5aa038
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427600B2

Linked notes

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