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Preparation method of cefalonium

A technology of ceflonine and ceftiophene acid, which is applied in the field of preparation of ceflonine, can solve the problems of too many three wastes and cannot meet the requirements of industrialized production, and achieves the effects of less discharge of three wastes, being beneficial to the protection of production equipment, and fast drying

Active Publication Date: 2015-06-24
QILU SYNVA PHARMA
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  • Description
  • Claims
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Problems solved by technology

Although the yield of the above-mentioned technical scheme has been improved and the price of raw materials has been reduced, there are more three wastes produced, and the yield still cannot meet the requirements of industrial production

Method used

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  • Preparation method of cefalonium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A preparation method of cefaroline, the steps are as follows:

[0035] (1) Add 43.7g cephalothin acid to 300ml dichloromethane, heat to reflux, add 1ml trimethylchlorosilane, 35ml hexamethyldisilazane, and continue the reflux reaction for 10 hours; cool down, add 30ml N,N -Diethylaniline, stirred for 30 minutes; added 33g iodotrimethylsilane, reacted at room temperature for 3 hours, detected 7-ACA residue, 7-ACA<0.5%, the reaction was over; cooled the system, added 27g isonicotinamide, 100ml di Chloromethane, reacted for 3 hours to obtain 4-amino-1-(8-oxo-7-(2-((2-thienyl)acetamido)-2-(trimethylsilyl)oxy)carbonyl )5-azabicyclo[4.2.0]thio-2-octen-3-yl)methyl)pyridinium salt (compound of formula 4);

[0036] (2) To the 4-amino-1-(8-oxo-7-(2-((2-thienyl)acetamido)-2-(trimethylsilyl)oxy group prepared in step (1) )carbonyl)5-azabicyclo[4.2.0]thio-2-octen-3-yl)methyl)pyridinium salt (compound of formula 4) was added dropwise methanol 35ml, and the mass concentration was 30...

Embodiment 2

[0039] A preparation method of cefaroline, the steps are as follows:

[0040] (1) Add 43.7g cephalothinic acid to 350ml dichloromethane, heat to reflux, add 1ml trimethylchlorosilane, 40ml hexamethyldisilazane, continue to reflux for 10 hours; cool down, add 28ml N,N -Diethylaniline, stirred for 30 minutes; added 35g iodotrimethylsilane, reacted at room temperature for 3 hours, detected 7-ACA residue, 7-ACA<0.5%, the reaction was over; cooled the system, added 24g isonicotinamide, 120ml di Chloromethane, reacted for 4 hours to obtain 4-amino-1-(8-oxo-7-(2-((2-thienyl)acetamido)-2-(trimethylsilyl)oxy)carbonyl )5-azabicyclo[4.2.0]thio-2-octen-3-yl)methyl)pyridinium salt (compound of formula 4);

[0041] (2) To the 4-amino-1-(8-oxo-7-(2-((2-thienyl)acetamido)-2-(trimethylsilyl)oxy group prepared in step (1) )carbonyl)5-azabicyclo[4.2.0]thio-2-octen-3-yl)methyl)pyridinium salt (Formula 4 compound) in the reaction system dropwise added methanol 34ml, added 26gFeCl 3 , 88ml of 6N...

Embodiment 3

[0044] A preparation method of cefaroline, the steps are as follows:

[0045] (1) Add 43.7g cephalothin acid to 290ml dichloromethane, heat to reflux, add 1ml trimethylchlorosilane, 38ml hexamethyldisilazane, continue to reflux for 10 hours; cool down, add 29ml N,N -Diethylaniline, stirred for 30 minutes; added 36g iodotrimethylsilane, reacted at room temperature for 3 hours, detected 7-ACA residue, 7-ACA<0.5%, the reaction was over; cooled the system, added 26g isonicotinamide, 100ml di Chloromethane, reacted for 3.5 hours to obtain 4-amino-1-(8-oxo-7-(2-((2-thienyl)acetamido)-2-(trimethylsilyl)oxy)carbonyl )5-azabicyclo[4.2.0]thio-2-octen-3-yl)methyl)pyridinium salt (compound of formula 4);

[0046] (2) To the 4-amino-1-(8-oxo-7-(2-((2-thienyl)acetamido)-2-(trimethylsilyl)oxy group prepared in step (1) ) carbonyl) 5-azabicyclo [4.2.0] thio-2-octen-3-yl) methyl) pyridinium salt (formula 4 compound) in the reaction system dropwise added methanol 33ml, adding 12ml mass concen...

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Abstract

The invention relates to a preparation method of cefalonium. According to the preparation method, raw materials (cefalotin and pyrazinamide) react at a low temperature to obtain the product cefalonium. The preparation method particularly comprises the following steps: dissolving cefalotin acid into an organic acid, carrying out carboxyl protection by using a silanization protection reagent and then carrying out iodination reaction on reaction products and iodotrimethylsilane; then carrying out amination reaction on the reaction product from the former step and pyrazinamide; and finally carrying out deprotection by alcoholysis, regulating the pH value at a low temperature and crystalizing to obtain cefalonium. According to the preparation method of cefalonium, cefalotin acid is protected by the silanization protection reagent in an organic solvent and then reacts with iodotrimethylsilane; the reaction time is short, the reaction conditions are mild, the reaction is complete and no side reaction is almost generated; due to adoption of a mixed solvent crystallization method, the characteristics of high drying speed, light color and high yield can be achieved; in addition, the used solvent can be recycled and the amount of generated sewage can be reduced; therefore, the preparation method of cefalonium has remarkable economic and environmental benefits and facilitates industrial production.

Description

technical field [0001] The invention relates to a preparation method of cefuroxime, in particular to a preparation method of synthesizing cefuroxime from cephalothinic acid, and belongs to the technical field of veterinary drug synthesis. Background technique [0002] Cefuroning, Chinese alias (6R,7R)-3-[(4-formamido-1-pyridine)methyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino] -5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid inner salt. It is mainly used for the prevention and treatment of mastitis in the dry period of dairy cows. The drug belongs to long-acting broad-spectrum antibiotics, which can effectively treat and prevent various bacterial infections of dairy cows during the dry period. At present, there is no suitable method for industrialized production of cefuroxime. [0003] Chinese patent document CN103242346A (Application No. 201310189258.6) discloses a preparation method of ceftaroline, which uses 7-ICAC and thiopheneacetyl chloride as raw materials and r...

Claims

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Application Information

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IPC IPC(8): C07D501/46C07D501/04
CPCC07D501/04C07D501/46
Inventor 孙振苏玉辉王秀龙刘全才孔梅吴连勇
Owner QILU SYNVA PHARMA
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