[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]1To 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%).
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