Reaktion #167679

Reaktionsgleichung

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

Lösungsmittel

N,N-dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe 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
   SonstigeThe water layer was separated
5. 5
   Waschenwashed multiple times with ethyl acetate
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe crude material was purified by silica gel chromatography
8. 8
   Wascheneluting with a gradient of 10% to 50% of ethyl acetate in hexane

Vorschrift

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)+.

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