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

HRID 47829

반응식

HRID 47829 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cc7b8687c16a426eb76b3fa7fe5fd6a6
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699904B2

연결된 노트

불러오는 중…