With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17347-61-4,2,2-Dimethylsuccinicanhydride,as a common compound, the synthetic route is as follows.
General procedure: Compound 5 (16 mg, 0.032 mmol), 2,2-dimethyl succinic anhydride(41 mg, 0.32 mmol), DMAP (8 mg, 0.064 mmol), and pyridine (1.5 mL)were placed in a 10 mL glass tube and sealed. The mixture was stirred at120 C for about 12 h. The reaction mixture was then transferred into a50 mL flask. Pyridine was removed under reduced pressure. HCl (3 N,10 mL) was added, the mixture was extracted three times with EtOAc,and the organic layer washed with 3 N HCl for a second time. Then theorganic layer was washed with brine, dried over anhydrous Na2SO4,and concentrated in vacuo. The residue was purified by silica gelcolumn chromatography (hexane/EtOAc as eluent) to provide targetproduct 7 (11 mg). White solid, yield: 54%. 1H NMR (CDCl3, 400 MHz,ppm) delta: 4.76 (d, 1H, J=12 Hz, CH-OCO), in C3), 4.73 (s, 1H, C=CH,in C29), 4.60 (s, 1H, C=CH, in C29), 4.51-4.67 (m, 1H, CH-F, in C2),3.66 (s, 3H, CO2CH3), 2.92-2.98 (m, 1H, in C19), 2.62-2.76 (2d,J=16 Hz, CO-CH2-C(CH3)2), 2.17-2.23 (m, 3H, in C18 and C22),1.87-1.90 (m, 2H, in C1), 1.67 (s, 3H, CH3, in C30), 1.32 (s, 6H, 2CH3,CO2H-C(CH3)2-CH2-), 0.90 (s, 3H, CH3), 0.88 (s, 3H, CH3), 0.86 (s, 3H,CH3), 0.83 (s, 3H, CH3), 0.81 (s, 3H, CH3). 13C NMR (150 MHz, CDCl3) delta 176.50 (s), 176.23 (s), 170.83 (s), 150.27 (s), 109.60 (s), 89.47 (d,J=173.2 Hz), 81.47 (d, J=15.1 Hz), 56.38 (s), 54.89 (s), 51.13 (s),50.28 (s), 49.28 (s), 46.85 (s), 44.40 (d, J=17.8 Hz), 42.32 (s), 40.60(s), 39.42 (d, J=6.9 Hz), 38.55 (d, J=10.2 Hz), 38.01 (s), 36.80 (s),33.89 (s), 31.98 (s), 30.42 (s), 29.47 (s), 28.13 (s), 25.33 (s), 25.26 (s),25.16 (s), 24.92 (s), 20.93 (s), 19.17 (s), 18.02 (s), 17.39 (s), 17.14 (s),15.81 (s), 14.51 (s). 19F NMR (CDCl3, 376 MHz, ppm) delta: -190.57. ESIHRMS(m/z): calcd for C37H57FO6 [M+H]+: 617.4217, found617.4169.
As the paragraph descriping shows that 17347-61-4 is playing an increasingly important role.
Reference£º
Article; Li, Jizhen; Chang, Ling-Chu; Hsieh, Kan-Yen; Hsu, Pei-Ling; Capuzzi, Stephen J.; Zhang, Ying-Chao; Li, Kang-Po; Morris-Natschke, Susan L.; Goto, Masuo; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry; vol. 27; 13; (2019); p. 2871 – 2882;,
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