تفاعل #1983296

معادلة التفاعل

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

المذيبات

N,N-dimethylformamide

water

ظروف التفاعل

المعالجة

1. 1
   تركيزThe mixture was concentrated
2. 2
   workup.ADDITIONethyl acetate was added
3. 3
   workup.ADDITION1 N HCl was then added slowly until the pH=6
4. 4
   أخرىThe water layer was separated
5. 5
   غسيلwashed multiple times with ethyl acetate
6. 6
   تركيزconcentrated
7. 7
   أخرىThe crude material was purified by silica gel chromatography
8. 8
   غسيلeluting with a gradient of 10% to 50% of ethyl acetate in hexane

الإجراء التجريبي

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. 1 N 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, 1 H), 8.17 (s, 1 H), 7.69 (s, 1 H), 3.36-3.90 (m, 4 H), 2.97-3.29 (m, 2 H), 2.88 (dd, J=8.92, 3.37 Hz, 1 H), 2.18-2.47 (m, 2 H), 1.41 (s, 9 H); MS (DCI+) m/z 434.1 (M+H)+.

المصدر