Preparation method of 4-oximide-5'-(2-methylpropionyl) uridine
A technology of methyl propionyl and uridine is applied in the field of preparation of 4-oxime-5`-(2-methylpropionyl) uridine, and can solve the problems of low yield, high cost, difficult purification and the like, and achieves Simple preparation conditions, good crystallinity, good conversion and atom economy
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Embodiment 1
[0039] In a 500 ml three-necked reaction flask, sequentially add 18.8 g of compound 1, 40.7 g of 2,2-dimethoxypropane, and 188.0 mL of acetone. The system is stirred at room temperature, and then 8.0 g of sulfuric acid is added dropwise, and the system is stirred at room temperature for 2 hours. TLC (thin-layer chromatography) showed that the conversion of the raw material was complete, filtered, and the filter cake was rinsed with 100.0 ml of acetone to obtain 28.1 g of the product 2`,3`-O-isopropylidene cytidine sulfate (compound 2). Yield: 95.25%, off-white solid.
Embodiment 2
[0041] Add 50.0 g of compound 2 into a 500 ml reaction flask, followed by adding 150 mL of anhydrous acetonitrile, 3.3 g of DMAP and 41.0 ml of DBU in sequence, stirring at room temperature, then adding 54.0 ml of isobutyric anhydride dropwise, and stirring the system at 60°C for 3 hours , TLC showed that the conversion of raw materials was complete, then the temperature was lowered, acetonitrile was removed by distillation under reduced pressure, 300.0 ml of dichloromethane and 200.0 ml of saturated sodium bicarbonate were added to the oil, and the layers were separated, and the dichloromethane layer was extracted with 200.0 ml of dilute hydrochloric acid (1M). Once, the dichloromethane phase was collected, dried, and concentrated to obtain the product 2`,3`-O-(1-methyl-1-oxopropyl)-N-(2-methyl-1-oxopropyl )-5`-(2-methylpropionyl)uridine (compound 3) 49.9 g, yield: 89.88%, off-white solid.
Embodiment 3
[0043] Add 50.0 g of compound 3 into a 500 ml reaction flask, add 200.0 mL of isopropanol, 100.0 ml of water, and 7.3 ml of 50% hydroxylamine aqueous solution in sequence, and stir the system at 80°C for 20 hours. TLC shows that the conversion of the raw materials is complete, and then cool down , distilled off isopropanol under reduced pressure, added 200.0 ml of ethyl acetate and 200.0 ml of saturated aqueous sodium chloride solution to the oily matter, separated layers, extracted the ethyl acetate layer twice with 200.0 ml of water, collected the ethyl acetate phase, dried, and concentrated , the yellow crude product was obtained, and the product 2`,3`-O-(1-methyl-1-oxopropyl)-4-oxime-5`-( 2-methylpropionyl)uridine (compound 4), 37.5 g, yield: 85.91%, white solid.
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