A kind of method for preparing the key intermediate compound of trabectedin
A technology of trabectedin and compounds, applied in the field of organic synthesis, can solve the problems of cumbersome post-treatment, large amount of pyridinium salt, harsh reaction conditions, etc., and achieve the effect of simple post-treatment purification, cheap and easy-to-obtain raw materials, and mild reaction conditions
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Embodiment 1
[0029] Compound II (134mg, 0.21mmol) was dissolved in acetonitrile (ml) and a freshly configured buffer solution (prepared by dissolving 60mg of sodium acetate in 6ml of acetic acid), and adding anhydrous zinc sulfate (24mg), Anhydrous sodium glyoxylate (242mg), after replacing the argon protection, the resulting reaction solution was stirred and reacted at 15°C. After the reaction was monitored by TLC, diethyl ether (225ml) was added to the reaction solution, and the organic phase was washed with distilled water (15ml×3) , after separation, the aqueous phase was extracted with dichloromethane (30ml×3), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated below 50°C to obtain crude compound I (132mg) as a yellow solid. The crude compound I was pulverized and stirred in n-hexane (2ml) at room temperature, filtered and dried to obtain off-white pure compound I (119 mg, 91%). The NMR characterization information of the obtained pure co...
Embodiment 2
[0031] Compound II (50g, 80.3mmol) was dissolved in acetonitrile (780ml) and a newly configured buffer solution (made by dissolving 5.46g sodium acetate in 780ml acetic acid), and anhydrous zinc sulfate (6.48g , 40.1mmol), anhydrous sodium glyoxylate (77.10g, 0.8mol), after replacing the argon gas protection, the resulting reaction solution was stirred at 10°C for reaction, and after the reaction was monitored by TLC, diethyl ether (15.6L) was added to the reaction solution, The organic phase was washed with distilled water (780ml×2). After separation, the aqueous phase was extracted with dichloromethane (1560ml×3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated below 50°C to obtain a yellow solid Crude compound I (50 g). The crude compound I was pulverized and stirred in n-hexane (1000ml) at room temperature, filtered and dried to obtain off-white pure compound I (47.45g, yield 95%). The NMR characterization information of t...
Embodiment 3
[0033]Compound II (1g, 1.6mmol) was dissolved in acetonitrile (7ml), DMSO (7ml) and a newly configured buffer solution (prepared by dissolving 180mg of sodium acetate in 36ml of acetic acid), and adding sulfuric acid heptahydrate to the reaction system Zinc (138g, 0.48mmol), sodium glyoxylate monohydrate (912mg, 8.0mmol), nitrogen replacement protection, the resulting reaction solution was stirred at 30 ° C for reaction, TLC monitoring after the completion of the reaction, the reaction solution with dichloromethane (1900ml ) was diluted, and the organic phase was washed with distilled water (280ml×2). After liquid separation, the aqueous phase was extracted with ethyl acetate (190ml×2). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated below 50°C Crude compound I (1.0 g) was obtained as a yellow solid. The crude compound I was pulverized and stirred in n-heptane (5×2ml) at room temperature, filtered and dried to obtain off-white ...
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