Gemfibrozil → Gemfibrozil Succinimide

HRID 32337

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-83f6f1e171f2410d9012f6843e85c92c
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427600B2

Linked notes

Loading…