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Synthesis method of cefotiam hexetil process impurity
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A kind of cefotiam pivoxil and technology of synthesis method, applied in the field of medicine
Active Publication Date: 2016-09-28
ZHEJIANG YONGNING PHARMA
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[0006] By consulting the literature, it is found that there is no literature report on the cefotiam process impurity 2-(2-(2-(2-(2-(2-aminothiazol-4-yl)-acetamido)thiazol-4-yl )-acetamido)thiazol-4-yl)acetic acid preparation
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Embodiment 1
[0021] Add 15.8g (0.1mol) of 2-amino-4-thiazoleacetic acid, 44g (0.25mol) of 2-amino-4-thiazole acetyl chloride, and 268ml of water in sequence in the reaction flask, add 35ml of triethylamine, and put the reaction flask into In a microwave reactor, react at 125°C for 20 minutes, adjust the pH to 3.0 with 1N concentrated hydrochloric acid, precipitate a light yellow solid, filter, and wash the filter residue with water and acetone in sequence to obtain 39.4 g of the light yellow target product, with a yield of 90% and a liquid phase purity of 99.6 %. 1 H-NMR (DMSO-d 6 ):6.98(s,1H),6.95(s,2H),6.73(s,1H),6.31(s,1H),3.92(s,2H),3.54(s,2H),3.32(s,2H) . 13 C-NMR (DMSO-d 6 ):172.7,168.8,168.7,168.6,158.0,157.8,148.4,145.3,145.1,110.5,106.2,103.4,41.7,38.6,38.3.LC-MS[M+H] + :439.0.
[0025] Add 15.8g (0.1mol) of 2-amino-4-thiazoleacetic acid, 44g (0.25mol) of 2-amino-4-thiazole acetyl chloride, and 268ml of water in sequence in the reaction flask, add 35ml of triethylamine, and put the reaction flask into In an oil bath, react at 125°C for 20 minutes, adjust the pH to 3.0 with 1N concentrated hydrochloric acid, precipitate a light yellow solid, filter, and wash the filter residue with water and acetone in sequence to obtain 0.9 g of the light yellow target product, with a yield of 2% and a liquid phase purity of 92.5% .
Embodiment 3
[0027] Add 15.8g (0.1mol) of 2-amino-4-thiazoleacetic acid, 44g (0.25mol) of 2-amino-4-thiazole acetyl chloride, and 268ml of water in sequence in the reaction flask, add 35ml of triethylamine, and put the reaction flask into In an oil bath, react at 125°C for 12 hours, adjust the pH to 3.0 with 1N concentrated hydrochloric acid, precipitate a light yellow solid, filter, and wash the filter residue with water and acetone successively to obtain 8 g of the light yellow target product, with a yield of 22.5% and a liquid phase purity of 92.7%.
[0028] Through the comparison of Example 1, Example 2, and Example 3, it is found that microwave-assisted catalysis significantly improves the reaction rate and yield.
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Abstract
The invention belongs to the technical field of medicine, and mainly relates to a preparation method of a cefotiam hexetil process impurity of 2-(2-(2-(2-(2-(2-aminothiazole-4-yl)-acetamido) thiazole-4-yl)-acetamido) thiazole-4-yl) acetic acid. According to the method, 2-amino-4-thiazoleacetic acid and 2-amino-4-thiazole acetyl chloride are used as raw materials to be dissolved into a solvent; microwaves are used for assisting the base catalysis reaction; the pH is regulated to an acid state; filtration and washing are performed to obtain the 2-(2-(2-(2-(2-(2-aminothiazole-4-yl)-acetamido) thiazole-4-yl)-acetamido) thiazole-4-yl) acetic acid, i.e., the cefotiam hexetil process impurity. The reaction equation is shown as the accompanying drawing. Therefore the method has the characteristics that the reaction time is short; the synthesis operation is simple and convenient; the purification operation is easy; the yield is high; the purity is high; the product can be used as a necessary product of cefotiam hexetil quality control or can be applied to the cefotiam hexetil impurity reference substance study, and the like.
Description
technical field [0001] The invention belongs to the technical field of medicine, and mainly relates to a process impurity of cefotiam pivoxil: 2-(2-(2-(2-(2-(2-aminothiazol-4-yl)-acetamido)thiazole-4 -yl)-acetamido)thiazol-4-yl)acetic acid preparation method. Background technique [0002] Cefotiam was first developed by Takeda Pharmaceutical Co., Ltd., Japan. This strain is an oral antibiotic produced by esterification of cefotiam ethyl for injection. Its structural formula is: [0003] [0004] This product itself has no antibacterial effect, and is rapidly hydrolyzed into cefotiam (CTM) in the intestinal mucosa after oral administration and absorbed. The antibacterial activity of CTM against Gram-positive and negative bacteria is the same as that of previous oral cephalosporins, and it is stable to β-lactamase. This product is clinically isolated Staphylococcus aureus, coagulase-negative Staphylococcus pneumoniae, Streptococcus pneumoniae, Neisseria gonorrhoeae, Ampi...
Claims
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