반응 #167679

반응 방정식

1,2-Dichloro-4-fluoro-5-nitrobenzene

2-(4-(tert-butoxycarbonyl)piperazin-2-yl)acetic acid

Triethylamine

→

title compound

2-(4-(tert-butoxycarbonyl)-1-(4,5-dichloro-2-nitrophenyl)piperazin-2-yl)acetic acid

용매

N,N-dimethylformamide

water

반응 조건

후처리

1. 1
   농축The mixture was concentrated
2. 2
   workup.ADDITIONethyl acetate was added
3. 3
   workup.ADDITION1N HCl was then added slowly until the pH=6
4. 4
   기타The water layer was separated
5. 5
   세척washed multiple times with ethyl acetate
6. 6
   농축concentrated
7. 7
   기타The crude material was purified by silica gel chromatography
8. 8
   세척eluting with a gradient of 10% to 50% of ethyl acetate in hexane

실험 절차

1,2-Dichloro-4-fluoro-5-nitrobenzene (0.125 mL, 0.952 mmol) and 2-(4-(tert-butoxycarbonyl)piperazin-2-yl)acetic acid (256 mg, 1.048 mmol) were dissolved in N,N-dimethylformamide (2 mL) and water (1 mL). Triethylamine (0.398 mL, 2.86 mmol) was slowly added. The resulting mixture was heated at 50° C. overnight. The mixture was concentrated and ethyl acetate was added. 1N HCl was then added slowly until the pH=6. The water layer was separated and washed multiple times with ethyl acetate. The organic layers were then combined and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient of 10% to 50% of ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.32 (br, 1H), 8.17 (s, 1H), 7.69 (s, 1H), 3.36-3.90 (m, 4H), 2.97-3.29 (m, 2H), 2.88 (dd, J=8.92, 3.37 Hz, 1H), 2.18-2.47 (m, 2H), 1.41 (s, 9H); MS (DCI+) m/z 434.1 (M+H)+.

출처