C13-C18-bit double-bond oleanolic acid type compound and preparation method and application thereof
A C13-C18, oleanolic acid technology, applied in steroids, digestive system, organic chemistry, etc., can solve problems such as less impact
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Embodiment 1
[0052] Synthesis of compound 1
[0053] synthetic route:
[0054]
[0055] Synthesis of the first step 13V-CDDO
[0056] Feeding see Table 1.
[0057] Table 1:
[0058]
[0059] Operation process:
[0060] Add 0.5g of 13OH-CDDO to a 50mL single-necked bottle, dissolve it with 15mL of acetonitrile, add 4mL of concentrated sulfuric acid to react for 10h under stirring; after the reaction solution is detected by TLC, add a small amount of water and extract with dichloromethane to obtain pure 13V-CDDO.
[0061] Synthesis of the second step 13V-CDDO-Me
[0062] Feeding see Table 2.
[0063] Table 2:
[0064]
[0065] Operation process:
[0066] Add 0.5g13V-CDDO to a 50mL single-necked bottle, dissolve it with 10mLTHF and 10mLDMF, add 0.1gNaH under stirring at -0°C, add 0.4mL methyl iodide after one hour, seal it, and stir overnight at room temperature in the dark; the reaction solution is tested by TLC After detection, the point with the least polarity is the produ...
Embodiment 2
[0071] Synthesis of compound 2
[0072] synthetic route:
[0073]
[0074] Feeding see Table 3.
[0075] table 3:
[0076]
[0077] Operation process:
[0078] Add 0.8g of 13V-CDDO to a 50mL single-necked bottle, dissolve it in 15mL of THF, add 1.5mL of oxalyl chloride under stirring at -0°C, and react for three hours under dry conditions, take it out and spin dry, remove the oxalyl chloride, then add 15mL of dichloromethane to dissolve , and finally join NH 3 / ethanol 6mL, sealed, and stirred overnight at -0°C; after the reaction solution was detected by TLC, it was subjected to flash column chromatography on a silica gel column to obtain the pure compound 2.
[0079] Characterization data of compound 2:
[0080] 1 H NMR (500MHz, DMSO-d 6 )δ8.66(s,1H),5.99(s,1H),3.32(s,4H),2.76(dd,J=13.6,2.4Hz,1H),2.42–2.31(m,1H),2.13(s ,1H),2.10–1.95(m,4H),1.85–1.64(m,4H),1.56(s,3H),1.44(s,1H),1.41(s,2H),1.36(s,3H), 1.33(s,1H),1.30(d,J=4.9Hz,1H),1.24(s,1H),1.19(s,1H),1.15(d,J=...
Embodiment 3
[0083] Synthesis of compound 3
[0084] synthetic route:
[0085]
[0086] Feeding see Table 4.
[0087] Table 4:
[0088]
[0089] Operation process:
[0090] Add 0.6g13V-CDDO to a 50mL one-mouth bottle, dissolve it in 15mLTHF, add 1.5mL oxalyl chloride under stirring at -0°C, and react for three hours under dry conditions, take it out and spin dry, remove oxalyl chloride, then add 20mLTHF to dissolve, and finally add Methylamine 6mL was sealed, and stirred overnight at -0°C; the reaction solution was tested by TLC, followed by flash column chromatography on a silica gel column to obtain pure compound 3.
[0091] Characterization data of compound 3:
[0092] 1 H NMR (500MHz, DMSO-d 6 )δ6.18(s,1H),5.06(s,1H),3.29(s,2H),2.78(dd,J=13.5,3.7Hz,1H),2.43–2.28(m,1H),2.00(t ,J=8.2Hz,2H),1.90–1.72(m,5H),1.66(d,J=11.2Hz,3H),1.46(d,J=13.2Hz,1H),1.41(s,3H),1.37 –1.26(m,6H),1.22(d,J=17.7Hz,2H),1.16(s,5H),1.09(d,J=11.7Hz,7H),0.98(s,3H),0.93(s, 4H).
[0093] 13 C NMR (126MHz...
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