Dimethylformamide → 2-[4-(2-Heptanoylamino-ethyl)-phenylamino]-2-methyl-propionic acid tert-butyl ester

HRID 47829

反応式

HRID 47829 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:25]([O:29][C:30](=[O:35])[C:31](Br)([CH3:33])[CH3:32])([CH3:28])([CH3:27])[CH3:26].CN(C)C=O>O>[C:25]([O:29][C:30](=[O:35])[C:31]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:7]=1)([CH3:33])[CH3:32])([CH3:28])([CH3:27])[CH3:26]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 86586371Heptanoic acid [2-(4-amino-phenyl)-ethyl]-amide

生成物 1

HCID 698844682-[4-(2-Heptanoylamino-ethyl)-phenylamino]-2-methyl-propionic acid tert-butyl ester収率 58.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

1H NMR (400 MHz, CDCl3) δ6.94 (d, 2H), 6.61 (d, 2H), 5.35 (s, 1H), 3.57 (s, 2H), 3.43 (m, 2H), 2.66 (t, 3H), 2.07 (t, 2H), 1.55 (m, 3H), 1.24 (m, 5H), 0.84 (t, 3H). A mixture of heptanoic acid [2-(4-amino-phenyl)-ethyl]-amide (1.50 g, 6.04 mmol), cesium carbonate (7.87 g, 24.2 mmol), tert butyl-2-bromoisobutyrate (10.78 g, 48.3 mmol) and dimethylformamide (14.6 mL) was heated at 80° C. for 4 days. The reaction mixture was cooled to ambient temperature, diluted with water and extracted with ether (2×). The combined organics were washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (2:3 ethyl acetate/hexanes) to provide 1.37 g (58%) of 2-[4-(2-heptanoylamino-ethyl)-phenylamino]-2-methyl-propionic acid tert-butyl ester as a colorless oil.

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with ether (2×)
  3. washThe combined organics were washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash column chromatography (2:3 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-cc7b8687c16a426eb76b3fa7fe5fd6a6
出典データセット
uspto-grants-2004_03
特許番号
US06699904B2

関連ノート

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