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

HRID 1064810ノート

反応式

HRID 1064810 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 522689Potassium Fluoride触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a97242acab8944488b23ce99ae3e3ffe
出典データセット
uspto-grants-2005_11
特許番号
US06969711B2

反応ノート

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