A kind of synthesis method of tulamycin residue marker
A technology of tulamycin and markers, which is applied in the field of synthesis of tulamycin residue markers, can solve the problems of many by-products, easy degradation reactions, instability of erythromycin A oxime, etc., and achieve reaction yield High, cheap raw materials, easy to obtain the effect of raw materials
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Embodiment 1
[0042] Dissolve 100g of erythromycin A(E) oxime in 400mL of acetone and 400mL of water, add 50g of sodium bicarbonate, and add 38g of p-toluenesulfonyl chloride at 0°C under stirring conditions (drip within 10min), continue stirring for 3h, use The reaction progress was monitored by thin layer chromatography (TLC). After the reaction is complete, use 20% NaOH to adjust the pH of the solution to 12, rise to room temperature, and stir for 30 minutes. At this time, a white solid is formed, which is filtered by suction, and the resulting product is dried in a vacuum oven at 50°C for 5 hours to obtain a red Mycin A6,9-imine ether 95g, yield >95%, melting point 129-131°C.
Embodiment 2
[0044] Dissolve 19g of erythromycin A6,9-imine ether in 200mL of methanol, add 8g of sodium borohydride in batches at -15°C, stir and react for 12h, after the reaction is complete, add 15g of citric acid, stir to dissolve, add 10% concentration of sulfuric acid solution until the pH value of the solution was 3, and the stirring reaction was continued for 1 h. After the reaction was completed, 20% sodium hydroxide was added to adjust the pH of the solution to alkaline, and a white solid was precipitated. After filtration, 16.5 g of azoerythromycin was obtained, with a yield of 87% and a melting point of 114-116°C.
Embodiment 3
[0046] (1) Dissolve 15 g of azoerythromycin prepared by the method of Example 2 in methanol solution, stir and dissolve at -5°C, add 4 mol / L sulfuric acid to adjust the pH value of the solution to 1-2, react for 6 hours, and the reaction is complete Afterwards, the pH of the solution was adjusted to 8-9 with 20% sodium hydroxide, extracted three times with an appropriate amount of dichloromethane, and the filtrate was collected and concentrated to obtain 7.2 g of crude TUM with a yield of 62%.
[0047] (2) Put 7.2g of crude TUM in a three-neck flask equipped with a spherical condenser, add 100mL of a mixed solution of acetone and petroleum ether, the volume ratio of acetone and petroleum ether is 8:1, stir and dissolve at 60°C for 2h, and then Cool to 0-5°C for recrystallization for 6 hours, filter, and dry the resulting product. According to this method, it was recrystallized twice again, and the obtained solid was dried in a vacuum oven at 50°C for 5 hours to obtain 3.9 g of...
PUM
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