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A technology for cefathiamidine and aminocephalosporanic acid is applied in the field of preparation of chemical raw material cefathiamidine, and can solve the problems of prolonged operation time, overflow phenomenon, unsatisfactory yield and the like
Inactive Publication Date: 2010-12-22
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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However, when producing cefathiamic acid in large quantities, the solvent system used is water-acetone, and the ratio of water is relatively large (2:1), which will hydrolyze bromoacetyl bromide and increase its consumption (1.3eq)
When dissolving 7-ACA with sodium bicarbonate, a large amount of foam will be generated, and the tank will overflow. You must wait for the foam to disappear before continuing to add sodium bicarbonate slowly, prolonging the operation time
Moreover, 7-ACA is unstabl
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Embodiment 1
[0028] Example 1 Synthesis of Cefathiamidine Acid
[0029] Add 50 ml of dichloromethane, 12 g (0.044 mol) of 7-ACA, and 11.2 g of BSA to a 250 ml round bottom flask, and stir at room temperature for 2 hours to dissolve. Then, 8.82g (0.044mol) of bromoacetyl bromide was slowly added dropwise at 0°C. After the dropwise addition, the reaction temperature can slowly rise to room temperature and react for 2h. 100ml of distilled water was added to the reaction solution, a large amount of solids precipitated, stirring was continued for half an hour, suction filtration, the filter cake was washed with water, and vacuum dried to obtain 15.56g of cefathiamidine acid. The yield was 90.2%.
Embodiment 2
[0030] Example 2 Synthesis of crude cefathiamidine
[0031] Add 3.93g cefathiamidine acid, 40ml dichloromethane, 1.3ml triethylamine into a 150ml round bottom flask, the solution becomes clear, add 1.6g N,N'-diisopropylthiourea, stir at room temperature for 3 hours, TLC The detection reaction is complete. Slowly add 50ml acetone dropwise, a solid precipitates, continue to stir for 2h, and let it stand for half an hour. Filter with suction and wash with acetone. After vacuum drying, 4.45 g of crude cefathiamidine was obtained. The yield was 94.1%.
Embodiment 3
[0032] Example 3 Refined crude cefathiamidine
[0033] Add 5g of crude cefathiamidine to a 100ml round bottom flask, dissolve it with 5ml of distilled water, adjust the pH to 5.5 with hydrochloric acid, add a certain amount of acetone until the solution becomes turbid, control the stirring speed, continue to slowly add 50ml of acetone, crystallize for 3h, filter with suction, and wash , Dried under vacuum to obtain 4.6g of cefathiamidine. The purity is 98.48%.
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Abstract
The invention relates to a preparation method of cefathiamidine, which comprises the following steps: (1) preparing cefathiamidine acid, performing silanization of 7-AC by BSA at room temperature, reacting with bromoacetyl bromide at zero DEG C, processing and separating out solid, filtering and drying to obtain high-purity cefathiamidine acid; (2) adding alkaline reagent to the cefathiamidine acid, reacting with N, N'-diisopropyl thiourea, adding slightly soluble solvent and separating out coarse cefathiamidine; and (3) dissolving the coarse cefathiamidine in a proper solvent, regulating the pH value of the solution to be between 4 and 5.5, adding the lightly soluble solvent until the solution is turbid, controlling the stirring speed, continuing slowly dripping the slightly soluble solvent, separating out the product, separating and drying to obtain the cefathiamidine. The method has the advantages of few steps, simple process, high purity and easy implementation.
Description
Technical field [0001] The invention relates to a preparation method of a chemical raw material medicine cefathiamidine, which belongs to the field of chemical medicine synthesis. Background technique [0002] Cefathiamidine (Cefathiamidine) is the first-generation cephalosporin, which is the first in my country and used clinically. [0003] [0004] Commonly known as: Pioneermycin 18, Cephalosporin 18. The antibacterial spectrum is similar to cephalothin. It has a strong effect on Staphylococcus aureus, Streptococcus viridans, and pneumococcus. It has unique antibacterial activity against Enterococcus. It is mainly used for respiratory tract infections caused by Staphylococcus aureus, pneumococcus and streptococcus. Biliary tract infection, urinary tract infection, gynecological infection, sepsis, pneumonia, meningitis and other infections. USP 3,646,025 and "Chinese Journal of Medicinal Chemistry", 2001, 10, No. 11, P293-294, and application number 200410102519.7 provide a meth...
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IPC IPC(8): C07D501/28C07D501/04C07D501/12
Inventor 冯文化李强邓愉凤
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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