反応 #167679

反応方程式

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

溶媒

N,N-dimethylformamide

water

反応条件

後処理

1. 1
   濃縮The 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
   その他The water layer was separated
5. 5
   洗浄washed multiple times with ethyl acetate
6. 6
   濃縮concentrated
7. 7
   その他The crude material was purified by silica gel chromatography
8. 8
   洗浄eluting with a gradient of 10% to 50% of ethyl acetate in hexane

実験手順

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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