A semi-synthetic taxane derivative and its preparation method and application
A technology of derivatives and taxanes, applied in the field of semi-synthetic taxane derivatives and their preparation and application
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Embodiment 1
[0052] Example 1 Preparation of compound II-1.
[0053]
[0054] 10-DAB (54.5 g, 100.0 mmol) was dissolved in dry tetrahydrofuran (1 L), under argon protection, acetic anhydride (100.0 mL, 1.0 mol) and cerium trichloride heptahydrate (1.86 g, 5.0 mol) were added under ice bath. mmol), slowly returned to room temperature, stirred and reacted for 3 h. After the reaction was detected by thin layer chromatography, the reaction solution was concentrated and evaporated to dryness. The resultant was diluted with ethyl acetate (1.5 L), followed by distilled water (500 mL×3), saturated chlorine Washed with an aqueous sodium chloride solution (500 mL×3), dried over anhydrous sodium sulfate, and concentrated to obtain a white solid crude product, which was recrystallized to obtain 56.0 g of a white solid product II-1 with a yield of 96.0%.
[0055] 1 H NMR (600 MHz, CDCl 3 ) δ 8.10 (d, J = 7.2 Hz, 2H), 7.61 (t, J = 7.8Hz, 1H), 7.48 (t, J =7.2 Hz, 2H), 6.32 (s, 1H), 5.62 (d, ...
Embodiment 2
[0056] Example 2 Preparation of compound III-1.
[0057]
[0058] Compound II-1 (51.5 g, 88.0 mmol) was dissolved in dry dichloromethane (1 L), under argon protection, dry pyridine (200.0 mL, 2.2 mol) was added, the reaction solution was cooled to -35 °C, slowly Trifluoromethanesulfonic anhydride (35.5 mL, 220.0 mmol) was added dropwise, and the addition was completed within 1 h, continued stirring for 4 h, slowly returned to room temperature and stirred overnight. After the reaction was detected by thin layer chromatography, the reaction solution was diluted with dichloromethane (2.5L) diluted, washed with 1M aqueous sodium hydrogen sulfate solution (750 mL×3), saturated aqueous sodium hydrogen carbonate solution (300 mL×3), and saturated aqueous sodium chloride solution (300 mL×3) successively, dried over anhydrous sodium sulfate, concentrated . The obtained orange-red solid crude product was dissolved in ethyl acetate / dichloromethane=1:2, and petroleum ether was added u...
Embodiment 3
[0060] Example 3 Preparation of compound IV-1.
[0061]
[0062] Compound III-1 (50.0g, 70.0mmol), sodium chloride (80.0g) and 4Å molecular sieve (30.0g) were dissolved in dry acetonitrile / tetrahydrofuran=(1000mL / 100mL), under argon protection, before room temperature After stirring for 1 h, the temperature was raised to 75°C and the reaction was continued for 2 h. After the reaction was detected by thin layer chromatography, the reaction solution was suction filtered, the filter cake was rinsed with a large amount of ethyl acetate, the filtrate was evaporated to dryness, and ethyl acetate (1.5 L) Dissolved, washed with saturated aqueous sodium bicarbonate solution (300 mL×3) and saturated aqueous sodium chloride solution (300 mL×3) successively, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography (dichloromethane / ethyl acetate=10: 1) 36.9 g of white solid product IV-1 was obtained, with a yield of 91.0%.
[0063] 1 H NMR (600 MHz, CD...
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