Aryl ether-substituted oxazolidinone carboxylic ester derivative, preparation method and applications thereof
A technology of oxazolidinone carboxylic acid and derivatives, which is applied in the direction of medical preparations containing active ingredients, drug combinations, and pharmaceutical formulas, and can solve the problems of non-recyclable chemical waste, low atom economy, and cumbersome synthesis steps, etc. problem, achieve the effect of low cost, few steps and high atom economy
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Embodiment 1
[0073] The preparation of embodiment 1 compound a
[0074] The structure of compound a is shown below:
[0075]
[0076] The preparation process is:
[0077] (1) P-bromophenol (0.40mmol), (acetonitrile) [(2-biphenyl) di-tert-butylphosphine] gold (I) hexafluoroantimonate (5.0mol%), Molecular sieves were dissolved in 4.0 mL of dry dichloromethane to prepare mixed solution A;
[0078] (2) Diazoacetate (0.48mmol) and 3-(1,3-propadiene)-2-oxazolidinone (0.48mmol) were dissolved in 2.0mL of dry dichloromethane to prepare mixed solution B;
[0079] (3) At room temperature, add the mixed solution B to the aforementioned mixed solution A with a syringe pump for 1 hour; at the same time, stir vigorously; after the mixed solution B is added dropwise, continue to stir at room temperature for 60 minutes.
[0080] After the reaction is finished, filter and obtain the filtrate to remove the solvent by rotary evaporation, then the crude product is purified by column chromatography to o...
Embodiment 2
[0082] The preparation of embodiment 2 compound b
[0083] The structure of compound b is shown below:
[0084]
[0085] The preparation process refers to Example 1, the difference is that phenol is used instead of p-bromophenol, and compound b can be prepared as a colorless oil with an isolated yield of 66%. the product of 1 H NMR schematic as Figure 4 As shown, its 13 C NMR schematic as Figure 5 shown.
[0086] 1 H NMR (400MHz, CDCl 3 )δ7.57(dd,J=5.3,3.3Hz,2H),7.39–7.33(m,2H),7.33–7.28(m,1H),7.21–7.15(m,2H),6.93(t,J= 7.4Hz, 1H), 6.78(dd, J=8.7, 0.9Hz, 2H), 6.48(d, J=14.4Hz, 1H), 4.55(dt, J=14.5, 7.4Hz, 1H), 4.33(t, J=8.2Hz, 2H), 3.70(s, 3H), 3.59–3.47(m, 2H), 3.23(ddd, J=14.8, 7.9, 0.8Hz, 1H), 3.11(ddd, J=14.8, 6.9, 1.1Hz,1H). 13 C NMR (101MHz, CDCl 3 )δ172.1, 155.2, 155.1, 138.7, 129.2, 128.5, 128.1, 127.1, 126.1, 121.9, 118.2, 103.1, 84.9, 62.1, 52.8, 42.4, 37.56. HRMS (ESI) [M+Na] + calcd for C 21 h 21 NO 5 ,390.1312,found 390.1312.
Embodiment 3
[0087] The preparation of embodiment 3 compound c
[0088] The structure of compound c is shown below:
[0089]
[0090] The preparation process refers to Example 1, the difference is that p-phenylphenol is used instead of p-bromophenol, and compound c can be prepared as a white solid with an isolated yield of 88%. the product of 1 H NMR schematic as Figure 6 As shown, its 13 CNMR schematic diagram as Figure 7 shown.
[0091] 1 H NMR (500MHz, CDCl 3)δ7.59(d, J=7.8Hz, 2H), 7.50(d, J=7.8Hz, 2H), 7.41(d, J=8.7Hz, 2H), 7.38(t, J=7.7Hz, 4H) ,7.32(d,J=7.3Hz,1H),7.28(dd,J=13.8,6.3Hz,1H),6.84(d,J=8.7Hz,2H),6.54(d,J=14.3Hz,1H) ,4.59(dt,J=14.5,7.4Hz,1H),4.33(t,J=8.1Hz,2H),3.72(s,3H),3.60–3.49(m,2H),3.25(dd,J=14.8 ,7.9Hz,1H),3.14(dd,J=14.8,6.8Hz,1H). 13 C NMR (101MHz, CDCl 3 ( Na] + calcd for C 27 h 25 NO 5 ,466.1625,found 466.1628.
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