2,3-diaryl-2-propargyl acylamino-3-aryl amino methyl propionate derivative and preparation method and application thereof
A technology of methyl aryl aminopropionate and propargyl amido, which is applied in the field of synthetic medicine and chemical industry, and can solve the problems of unfavorable industrial synthesis of aryl-containing all-carbon chiral center compounds, harsh reaction conditions, chemical waste, and high cost. , to achieve the effect of low cost, few reaction steps and less waste
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Embodiment 1
[0052]
[0053] With imine (0.2mmol), rhodium acetate (0.002mmol), The mixture of molecular sieves (300 mg) was dissolved in 1.5 mL of dichloromethane solvent to prepare a mixed solution 1, which was stirred at 20° C. for 10 minutes. Then propargylamide (0.24mmol) and methyl phenyldiazoacetate (0.24mmol) were dissolved in 1.0mL dichloromethane solvent to prepare solution 2. Solution 2 was added to mixed solution 1 with a syringe pump at 20° C. within 1 hour. The reaction mixture was purified by flash column chromatography to obtain a pure product whose structure is shown in formula (a). Yield 75%, dr value equal to 95:5. of the product 1 H NMR schematic as figure 1 As shown, its 13 C NMR schematic as figure 2 shown.
[0054] 1 H NMR (400MHz, DMSO) δ9.22 (d, J = 17.2Hz, 2H), 7.28 (dd, J = 29.1, 25.1Hz, 8H), 7.08 (s, 2H), 6.58 (d, J = 7.3Hz ,1H),6.35(ddd,J=44.7,26.0,7.3Hz,3H),5.92(d,J=7.6Hz,1H),5.75(s,2H),5.33(d,J=7.7Hz,1H) ,4.35(s,1H),3.61(s,3H).
[0055] 13 C ...
Embodiment 2
[0057]
[0058] With imine (0.2mmol), rhodium acetate (0.002mmol), The mixture of molecular sieves (300 mg) was dissolved in 1.5 mL of dichloromethane solvent to prepare a mixed solution 1, which was stirred at 20° C. for 10 minutes. Then propargylamide (0.24mmol) and methyl phenyldiazoacetate (0.24mmol) were dissolved in 1.0mL dichloromethane solvent to prepare solution 2. Solution 2 was added to mixed solution 1 with a syringe pump at 20° C. within 1 hour. The reaction mixture was purified by flash column chromatography to obtain a pure product whose structure is shown in formula (b). Yield 87%, dr value equal to 89:11. of the product 1 H NMR schematic as image 3 As shown, its 13 C NMR schematic as Figure 4 shown.
[0059] 1 H NMR (400MHz, DMSO): δ9.59(s, 1H), 9.29(s, 1H), 8.08(d, J=13.0Hz, 2H), 7.69–7.18(m, 7H), 6.56(d, J =19.3Hz,1H),6.36(m,J=45.7,26.7,7.5Hz,3H),5.93–5.69(m,1H),5.60(d,J=8.0Hz,1H),4.36(s,1H) ,3.57(s,3H).
[0060] 13 C NMR (101MHz, DMSO) δ16...
Embodiment 3
[0062]
[0063] With imine (0.2mmol), rhodium acetate (0.002mmol), The mixture of molecular sieves (300 mg) was dissolved in 1.5 mL of dichloromethane solvent to prepare a mixed solution 1, which was stirred at 20° C. for 10 minutes. Then propargylamide (0.24mmol) and m-methoxyphenylmethyl diazoacetate (0.24mmol) were dissolved in 1.0mL of dichloromethane solvent to prepare solution 2. Solution 2 was added to mixed solution 1 with a syringe pump at 20° C. within 1 hour. The reaction mixture was purified by flash column chromatography to obtain a pure product whose structure is shown in formula (c). Yield 90%, dr value equal to 95:5. of the product 1 H NMR schematic as Figure 5 As shown, its 13 C NMR schematic as Figure 6 shown.
[0064] 1 H NMR (400MHz, DMSO): δ9.35(s, 1H), 9.26(s, 1H), 7.42(d, J=8.3Hz, 1H), 7.24(t, J=7.9Hz, 1H), 7.06( d,J=8.3Hz,1H),6.93(d,J=8.2Hz,1H),6.88(d,J=7.6Hz,1H),6.59(d,J=7.3Hz,1H),6.46(t, J=7.4Hz, 1H), 6.35(t, J=7.3Hz, 1H), 6.22(d, J=7....
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