2-Bromoethyl ethyl ether → 2-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,6-diisopropyl-3-(2-ethoxyethyloxy)phenyl)acetamide

HRID 1064810노트

반응식

HRID 1064810 반응식
[CH2:1]([O:3][CH2:4][CH2:5]Br)[CH3:2].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[S:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]([NH:28][C:29]2[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:32]=[C:31]([OH:38])[C:30]=2[CH:39]([CH3:41])[CH3:40])=[O:27])[CH2:21][CH2:20]1>[F-].[K+].C(#N)C>[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[S:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]([NH:28][C:29]2[C:34]([CH:35]([CH3:36])[CH3:37])=[CH:33][CH:32]=[C:31]([O:38][CH2:2][CH2:1][O:3][CH2:4][CH3:5])[C:30]=2[CH:39]([CH3:41])[CH3:40])=[O:27])[CH2:21][CH2:20]1

참가 물질

5

반응물 2

HCID 611412-Bromoethyl ethyl etherHCID 222726162-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide

생성물 1

HCID 222728062-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,6-diisopropyl-3-(2-ethoxyethyloxy)phenyl)acetamide수율 70%

시약·촉매·용매 2

HCID 522689Potassium Fluoride촉매HCID 6342Acetonitrile용매

실험 절차

2-Bromoethyl ethyl ether (2 ml) and potassium fluoride catalyst carried on alumina (40 wt %, 225 mg, 1.51 mmol) were added to a solution of 2-[4-[2-(benzoxazol-2ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide (150 mg, 0.30 mmol) in acetonitrile (3 ml) followed by stirring for 41 hours. The catalyst was filtered off and the filtrate was diluted with water and extracted with ethyl acetate. The organic layer was washed with a sodium chloride solution and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a preparative thin layer chromatography (developing solvent, chloroform:ammonia-saturated methanol=20:1) and the resulting crude crystals were recrystallized from ethyl acetate-hexane to provide 120 mg (yield 70%) of the desired compound as colorless powdery crystals.

후처리

  1. filtrationThe catalyst was filtered off
  2. additionthe filtrate was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by a preparative thin layer chromatography (developing solvent, chloroform:ammonia-saturated methanol=20:1)
  8. customthe resulting crude crystals were recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-a97242acab8944488b23ce99ae3e3ffe
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969711B2

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