The preparation method of aztreonam monocyclic nucleus

A technology of single-ring parent nucleus and aztreonam, which is applied in the field of preparation of aztreonam single-ring parent nucleus, can solve the problems of incomplete reaction, low yield and high production cost, so as to improve product quality and improve total yield , The effect of low production cost

Active Publication Date: 2011-12-21
SICHUAN WUSHENG CHUNRUI MEDICAL CHEM
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Problems solved by technology

The disadvantage of this process is that in the CBZ protection reaction, the reaction is not complete. Due to poor water solubility, the raw materials form a package, which affects the yield and product quality. The production cost is high and the yield is low.
[0012] Above-mentioned two kinds of preparation methods are when because of ring-closure reaction, operational route adopts tetrabutylammonium bisulfate to carry out ring-closure reaction, because tetrabutylammonium hydrogensulfate price is high, yield is low, and production cost is high

Method used

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  • The preparation method of aztreonam monocyclic nucleus
  • The preparation method of aztreonam monocyclic nucleus
  • The preparation method of aztreonam monocyclic nucleus

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Embodiment Construction

[0029] The method for preparing aztreonam monocyclic mother nucleus is as follows:

[0030]

[0031] 1) Take 200 kg of methanol with a weight percentage concentration of 99.5%, add 50 kg of threonine with a weight percentage concentration of 99.6%, cool to 3-5°C, add dropwise 50 kg of thionyl chloride with a weight percentage concentration of 99.2% , heated to the temperature of the solution is 35-45 ° C, reacted for 15-17 hours, after vacuum distillation, add 125 kg of 99.5% methanol, dropwise add saturated sodium carbonate solution, adjust the pH value of the solution to 7-8; 50 kg of benzyl chloroformate, reacted for 3-5 hours, and filtered to obtain 105 kg of β-hydroxy N-formyl benzyl threonine methyl ester;

[0032] 2) Add the β-hydroxy N-formylbenzyl threonine methyl ester obtained in step 1) into a reaction tank, add 200 kg of methanol, slowly pass through 50 kg of ammonia, react for 29-31 h, and distill under reduced pressure;

[0033] 3) Add 60 kg of 99.4% toluene...

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Abstract

The invention relates to a preparation method of aztreonam single-ring parent nucleus. The method uses benzyl chloroformate to protect under strong acidic conditions, and uses sodium carbonate to perform ring-closing reaction. The reaction is stable, the yield is greatly improved, and the total yield is For the 48% advantage.

Description

technical field [0001] The invention relates to a method for synthesizing medicine, in particular to a method for preparing aztreonam monocyclic mother nucleus. Background technique [0002] Aztreonam (also known as anthiamic acid monoamine, thioxime monoamide, and fungigram) is a fully synthetic monocyclic β-lactam antibiotic. Its antibacterial spectrum mainly includes Gram-negative bacteria, such as Escherichia coli, Klebsiella, Serratia, Proteus mirabilis, Haemophilus influenzae, Citrobacter, Pseudomonas aeruginosa, Neisseria gonorrhoeae, etc. Clinical medicinal use is mainly used for respiratory tract, lung infection, urinary tract infection, abdominal infection, bone and joint infection, skin and soft tissue inflammation, gynecological infection, and gonorrhea caused by sensitive Gram-negative bacteria. It can be used in meningitis because it can enter the cerebrospinal fluid. Because aztreonam has strong enzyme resistance and is not sensitive to other drugs, it is of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D205/085
Inventor 朱泽文胡奎郝庭格
Owner SICHUAN WUSHENG CHUNRUI MEDICAL CHEM
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