Dicyclohexylcarbodiimide → Naproxen Succinimide

HRID 32336

반응식

HRID 32336 반응식
[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

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 156391Naproxen

생성물 1

HCID 131727063Naproxen Succinimide

시약·촉매·용매 1

HCID 312751,4-Dioxane용매3회

반응 조건

온도
4 °C

실험 절차

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%)

후처리

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

출처 및 근거

ORD 기록
ord-cc2db437f6ba4274b59e4b03fd5aa038
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427600B2

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