Synthesis method of oseltamivir
A synthesis method and compound technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effects of simple operation, cheap and easy-to-obtain reagents, and short steps
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Embodiment 1
[0036] In a 50mL round-bottom flask, add the compound represented by structural formula I (1.54g, 11mmol) and the compound represented by structural formula II (1.5g, 10mmol), heat to 70℃ and react for 4 hours, then cool to room temperature and add Cu(OTf) 2 (181mg, 0.5mmol), PhI=NNs (4.2g, 10mmol), add 20mL of acetonitrile to dissolve, stir the reaction for 6 hours, stop the reaction, remove the solvent by rotary evaporation, and separate with silica gel (300-400 mesh) column chromatography. 3.2g of colored liquid, 67% yield. Colorless liquid 1 H-NMR(CDCl 3 ,600MHz): δ0.75(t,J=7.3Hz,3H),0.91(t,J=7.3Hz3H),1.23(t,J=7.1Hz,3H),1.35-1.39(m,2H),1.49 -1.53(m,2H),1.80-1.85(m,1H),2.56-2.60(m,1H),3.21-3.24(m,1H),3.26-3.30(m,1H),3.34-3.37(m, 1H), 3.40-3.42 (m, 1H), 4.11-4.20 (m, 2H), 4.61 (s, 1H), 4.78 (dd, J=11.4, 3.0Hz, 1H), 8.16 (d, J=9.2Hz) ,2H),8.45(d,J=8.4Hz,2H); 13 C-NMR(CDCl 3 ,150MHz): δ8.8,9.5,14.0,25.0,25.2,25.9,35.9,38.8,42.6,61.7,70.5,82.7,83.4,124.7,129.2,143.4,150.9,172.1...
Embodiment 2
[0045] Except that 50°C was used instead of 70°C in Example 1 to carry out the Diels-Alder reaction of the compound represented by structural formula I and the compound represented by structural formula II, the rest of the operation steps were the same as in Example 1, to obtain the total production of oseltamivir The rate was 13%, and the product characterization data were the same as in Example 1.
Embodiment 3
[0047] Except that 90°C was used instead of 70°C in Example 1 to carry out the Diels-Alder reaction of the compound represented by structural formula I and the compound represented by structural formula II, the rest of the operation steps were the same as in Example 1, to obtain the total production of oseltamivir The rate was 31%, and the product characterization data were the same as in Example 1.
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