Gemfibrozil → Gemfibrozil Succinimide

HRID 1943981Notes

Reaction equation

[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

Participants

Conditions

Temperature: 4 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-99aa1078cada41dbb1fb3818ba5879d7
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394813B2

Reaction notes

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