تفاعل #76107

معادلة التفاعل

heptanoic acid [2-(4-amino-phenyl)-ethyl]-amide

cesium carbonate

tert butyl-2-bromoisobutyrate

dimethylformamide

→

2-[4-(2-heptanoylamino-ethyl)-phenylamino]-2-methyl-propionic acid tert-butyl ester

المردود 58.1%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was cooled to ambient temperature
2. 2
   استخلاصextracted with ether (2×)
3. 3
   غسيلThe combined organics were washed with water and saturated aqueous sodium chloride
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىpurified by flash column chromatography (2:3 ethyl acetate/hexanes)

الإجراء التجريبي

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.

المصدر