Preparation method of norazithromycin
A technology of norazithromycin and erythromycin, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of reduced purity, small equipment investment, low production efficiency, etc., and reduce acidic ineffective decomposition , Slow down the release speed and save production cost
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reference example 1-1
[0046] Reference example 1-1: Preparation of erythromycin thiocyanate A oxime (III)
[0047] Add hydroxylamine hydrochloride (114g, 1.64mol) and 300g methanol to a 1000mL three-necked flask, stir at room temperature, and add triethylamine dropwise to adjust pH=6.3-6.7. Add erythromycin thiocyanate A(II) (200g, 0.25mol), raise the temperature to 30-35°C and react for 4h, add triethylamine dropwise during the reaction to adjust the pH=6.5±0.2; raise the temperature to 50-55°C, and continue to keep warm Reaction 48h. Cool down to 15-20°C, add 600mL deionized water dropwise, stir for 0.5h; crystallize at 0-5°C for 2h. Filter, wash with 200 mL of deionized water, and dry to obtain 180 g of white solid erythromycin A oxime thiocyanate (III). Yield 88.4%, melting point 182-185°C, purity 93.7% (HPLC).
reference example 1-2
[0048] Reference example 1-2: preparation of erythromycin thiocyanate A oxime (III)
[0049] Add hydroxylamine hydrochloride (228g, 3.3mol) and 600g methanol to a 2000mL three-necked flask, stir at room temperature, and add triethylamine dropwise to adjust the pH to 6.3-6.7. Add erythromycin thiocyanate A(II) (400g, 0.5mol), heat up to 30-35°C, and keep warm for 10h; add triethylamine dropwise during the reaction to adjust pH=6.5±0.2; heat up to 50-55°C, Continue the insulation reaction for 40h. Cool down to 15-20°C, add 1200mL deionized water dropwise, stir for 0.5h; 0-5°C, crystallize for 2h. Filter, wash with 400mL deionized water, and dry to obtain 348g of white solid erythromycin A oxime thiocyanate (III), with a yield of 87.0%, a melting point of 182-184°C, and a purity of 93.8% (see HPLC figure 1 and shown in Table 1).
[0050] The HPLC detection result of table 1 erythromycin A oxime thiocyanate
[0051] peak# keep time area area% high Separatio...
reference example 2
[0053] Reference example 2: Preparation of erythromycin A imine ether
[0054] Add erythromycin A oxime thiocyanate (III) (180 g, 0.22 mol) and 540 mL of acetone into a 2000 mL three-necked flask, and stir. 0-10°C, add 450g of 10% sodium bicarbonate solution, below 5°C, add p-toluenesulfonyl chloride (51g, 0.27moL) dropwise, after 1h, keep warm for 3h. 1200 mL of deionized water was added dropwise to the reaction solution, adjusted to pH=11-12 with 10 wt % NaOH aqueous solution, and stirred for 1 h. Crystallize at 0-5°C for 1h. Filter, wash with 400 mL deionized water at room temperature, and dry to obtain 142 g of white solid erythromycin A imine ether. Yield 88.3%, melting point 134-140 ℃, purity 92.9% (see HPLC figure 2 and shown in Table 2).
[0055] The HPLC detection result of table 2 erythromycin A imine ether
[0056] peak# keep time area area% high Separation Tailing factor Theoretical plate# 1 2.606 35405.142 2.508 4299 0.000 1...
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