تفاعل #1180765

معادلة التفاعل

[(5-phenyl-isoxazole-3-carbonyl)-amino]-acetic acid

DIPEA

HOBt

EDCI.HCl

4-(2bromo-phenoxy)-piperidine trifluoroacetate

→

5-phenyl-isoxazole-3-carboxylic acid {2-[4-(2-bromo-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide

المردود 35.0%

المذيبات

water

DMF

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe product was extracted with ethyl acetate
2. 2
   غسيلThe ethyl acetate layer was washed with brine solution
3. 3
   تجفيفdried over sodium sulfate
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   أخرىThe resulting residue was purified by column chromatography

الإجراء التجريبي

To a stirred solution of [(5-phenyl-isoxazole-3-carbonyl)-amino]-acetic acid (72.5 mg, 0.00026 mol) in DMF (1.5 mL) was added DIPEA (0.166 g, 0.00128 mol), HOBt (43.3 mg, 0.00032 mol) and EDCI.HCl (61.5 mg, 0.00032 mol) at ambient temperature. After 2 minutes 4-(2bromo-phenoxy)-piperidine trifluoroacetate (0.1 g, 0.00027 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel, 60-120 mesh (40% ethyl acetate in hexane) to afford 0.044 g (35%) of 5-phenyl-isoxazole-3-carboxylic acid {2-[4-(2-bromo-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 484.08 (M+1)+, 77.84%, 1H NMR (DMSO-d6): δ 8.63 (t, 1H), 7.98 (m, 2H), 7.6 (m, 4H), 7.4 (m, 2H), 7.2 (m, 1H), 6.9 (t, 1H), 4.8 (s, 1H), 4.3 (m, 2H), 3.5 (m, 4H), 1.5 (m, 4H).

المصدر