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A kind of synthetic method of cefotiam process impurity
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A synthesis method, technology of process impurities, applied in the field of medicine
Active Publication Date: 2019-01-08
ZHEJIANG YONGNING PHARMA
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[0005] By consulting the literature, it is found that no literature has reported the cefotiam process impurity 5-(((1H-tetrazol-5-yl-)mercapto)-methyl)-3-(2-aminoacetyl)-2-ylidene Preparation of methyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
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Embodiment 1
[0021] In the reaction flask, add 7-amino-3-[1-(2-methylamino)ethyl-1H-tetrazole-5-thiomethyl)-8-oxo-5-thia-1-nitrogen Heterobicyclo[4.2.0]oct-2-ene-2-carboxylic acid 50g (0.15mol), water 200ml, slowly add 20ml of concentrated hydrochloric acid, put the reaction bottle into a microwave reactor, react at 60°C for 15min, wash with saturated carbonic acid The pH of the sodiumhydrogen solution was adjusted to 5.5, and a pale yellow solid was precipitated. After filtration, the filter residue was washed with water and dichloromethane in sequence to obtain 40.8 g of the light yellow target product, with a yield of 83% and a liquid phase purity of 99.5%. 1 H-NMR (DMSO-d 6 ):4.72(s,2H),3.91(s,2H),3.56(s,2H),3.47(s,2H). 13 C-NMR (DMSO-d 6 ):195.0,170.4,150.0,139.6,131.5,126.9,68.4,30.9,29.5,25.1.LC-MS[M+H] + :329.0.
[0025] In the reaction flask, add 7-amino-3-[1-(2-methylamino)ethyl-1H-tetrazole-5-thiomethyl)-8-oxo-5-thia-1-nitrogen Heterobicyclo[4.2.0]oct-2-ene-2-carboxylic acid 50g (0.15mol), water 200ml, slowly add perchloric acid 38.5ml, put the reaction bottle into a microwave reactor, react at 60°C for 15min, use Saturated sodiumbicarbonate solution adjusted the pH to 5.5, precipitated a light yellow solid, filtered, and washed the filter residue with water and dichloromethane in sequence to obtain 26.1 g of the light yellow target product with a yield of 53% and a liquid phase purity of 98.5%.
Embodiment 3
[0027] In the reaction flask, add 7-amino-3-[1-(2-methylamino)ethyl-1H-tetrazole-5-thiomethyl)-8-oxo-5-thia-1-nitrogen Heterobicyclo[4.2.0]oct-2-ene-2-carboxylic acid 50g (0.15mol), water 200ml, slowly add glacial acetic acid 36.6ml, put the reaction bottle into a microwave reactor, react at 60°C for 15min, and use saturated The pH of the sodiumbicarbonate solution was adjusted to 5.5, and a light yellow solid was precipitated. After filtration, the filter residue was washed with water and dichloromethane in sequence to obtain 4.4 g of the light yellow target product, with a yield of 9% and a liquid phase purity of 93.5%.
[0028] By comparing Example 1 and Example 2, Example 3, we find that compared with perchloric acid and acetic acid, the reaction effect of concentrated hydrochloric acid is the best.
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Abstract
The invention belongs to the field of medicine, mainly relates to a synthetic method of cefotiam process impurities and provides a preparing method of cefotiam process impurities-5-(((1H-tetrazole-5-yl)sulfydryl)-methyl)-3-(2-amono acetyl)-2-methylene-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid. According to the method, 7-amino-3-[1-(2-methylamino)ethyl-1H-tetrazole-5-sulfomethyl)-8-oxo-5-sulfur-1-azabicyalo[4.2.0]-digoxin-2-alkene-2-carboxylic acid serves as a raw material and is dissolved in solvent, the microwave-assisted acid catalyzed reaction is carried out, the pH value is adjusted, and filtering and washing are carried out to obtain the target impurities. The method has the advantages that reaction time is short, synthetic operation is easy and convenient, purification operation is easy, the yield and the purity are high, and the impurities can serve as a necessity for controlling the quality of cefotiam or can be applied to cefotiam impurity comparison product study.
Description
technical field [0001] The invention belongs to the field of medicine, and mainly relates to cefotiam process impurity-5-(((1H-tetrazol-5-yl-)mercapto)-methyl)-3-(2-aminoacetyl)-2-methylene The preparation method of base-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid. Background technique [0002] Cefotiam, also known as (6R-trans)-7-[[(2-amino-4-thiazolyl)acetyl]amino]-3-[[[1-[(2-(Dimethylamino)ethyl Base]-1H-tetrazol-5-yl]thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid disalt Salt. It was first developed by Takeda Pharmaceutical Co., Ltd. in Japan. Its dihydrochloride is often used as a white or slightly yellow powder; it has a slightly specific odor; it dissolves effervescently with water to form a near-neutral transparent solution, slightly soluble in ethanol , insoluble in acetonechloroform. Cefotiam structural formula is: [0003] [0004] Since drug impurities are very important in drugprocess research, optimization and quality control, ...
Claims
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