Beta amino acid derivative as well as synthesis method and application thereof
A technology of amino acid and diacyl peroxide, which is applied in the direction of medical preparations containing active ingredients, drug combinations, chemical instruments and methods, etc., to achieve the effect of regulating cell apoptosis, regulating virus immunity, great clinical significance and market advantages
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Embodiment 1
[0102]
[0103] Add 0.75 mmol (1.5 equivalents) of compound 1-1, 0.5 mmol (1 equivalent) of lauroyl peroxide 1-2, 1 mmol (2 equivalents) of water, 2 mL of acetonitrile 1-3, 62.88 mg of catalyst Fe(OTf ) 3 (25mol%), 0.5mmol sulfuric acid (1 equivalent), add a magnetic stirrer, and then put it into a 60°C oil bath for 5 hours. After the reaction was completed, it was cooled to room temperature, concentrated by distillation under reduced pressure to remove the solvent, and the crude product was separated by column chromatography. The obtained product samples were marked as 1-4, a total of 169 mg, and the yield was 80%.
[0104] 1 H NMR (400MHz, CDCl 3 )δ7.79(d, J=7.7Hz, 3H), 7.66(s, 1H), 7.50–7.42(m, 2H), 7.33(d, J=8.5Hz, 1H), 7.18(d, J=8.8 Hz,1H),5.40(dd,J=8.9,4.9Hz,1H),3.50(s,3H),2.98–2.89(m,1H),2.10(s,3H),1.78–1.72(m,1H) ,1.61-1.60(m,1H),1.34–1.20(m,18H),0.88(t,J=6.8Hz,3H). 13 C NMR (100MHz, CDCl 3 )δ175.94,169.68,138.14,133.29,132.75,128.46,127.96,127.62,126.22,125.9...
Embodiment 2
[0106]
[0107] Add 0.75 mmol (1.5 equivalents) of compound 2-1, 0.5 mmol (1 equivalent) of peroxide 2-2, 1.0 mmol (2 equivalents) of water, 2 mL of acetonitrile 2-3, 37.73 mg of catalyst Fe (OTf ) 3 (15mol%), 0.5mmol sulfuric acid (1 equivalent), add a magnetic stirrer, and then put it into an 80°C oil bath to react for 5 hours. After the reaction was completed, it was cooled to room temperature, concentrated by distillation under reduced pressure to remove the solvent, and the crude product was separated by column chromatography. The obtained product sample was recorded as 2-4, a total of 190 mg, with a yield of 89%, dr=93:7.
[0108] The nuclear magnetic detection data of product sample 2-4 are as follows:
[0109] 1 H NMR (400MHz, CDCl 3 )δ7.16–7.00(m,4H),5.41(dd,J=8.9,5.0Hz,1H),3.55(s,3H),2.85(dt,J=8.9,5.7Hz,1H),2.06(s ,3H),1.76–1.65(m,1H),1.58–1.47(m,1H),1.29-1.25(m,18H),0.88(t,J=6.8Hz,3H). 13 C NMR (100MHz, CDCl 3 )δ175.50, 169.56, 161.14 (d, J C-F =245Hz), 13...
Embodiment 3
[0111]
[0112] Add 0.75 mmol (1.5 equivalents) of compound 3-1, 0.5 mmol (1 equivalent) of lauroyl peroxide 3-2, 1 mmol (2 equivalents) of water, 2 mL of acetonitrile 3-3, and 37.73 mg of catalyst Fe(OTf ) 3 (15mol%), 0.5mmol sulfuric acid (1 equivalent) was added to a magnetic stirrer, and then put into a 60°C oil bath for 5 hours of reaction. After the reaction was completed, it was cooled to room temperature, concentrated by distillation under reduced pressure to remove the solvent, and the crude product was separated by column chromatography. The obtained product samples were recorded as 1-4, a total of 156 mg, with a yield of 70%, dr=93:7.
[0113] 1 H NMR (400MHz, CDCl 3 )δ7.81(d,J=9.4Hz,2H),7.23-7.18(m,2H),5.49–5.38(m,1H),3.89(s,3H),3.58(s,3H),2.72–2.67 (m,1H),2.50(s,3H),2.03(s,3H),1.78-1.71(m,1H),1.50–1.45(m,1H),1.24(s,18H),0.88(t,J =6.9Hz,3H). 13 C NMR (100MHz, CDCl 3 )δ175.28,169.51,166.94,141.00,139.73,130.85,128.41,128.21,126.23,52.00,51.79,50.08,49.81,31...
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