Gemfibrozil → Gemfibrozil Succinimide

HRID 32337

반응식

HRID 32337 반응식
[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

참가 물질

5

반응물 3

HCID 3463GemfibrozilHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

생성물 1

HCID 86585518Gemfibrozil Succinimide

시약·촉매·용매 1

HCID 312751,4-Dioxane용매3회

반응 조건

온도
4 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-83f6f1e171f2410d9012f6843e85c92c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427600B2

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