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Synthesis method of aspoxicillin

A technology of apicillin and a synthesis method, applied in the field of chemical drug synthesis, can solve the problems of incomplete amino protection and removal, unsafe industrial production, reduced product yield and the like, and achieves overcoming poor reaction selectivity, less impurity residues, and by-products. less effect

Active Publication Date: 2014-09-24
HUNAN ER KANG PHARMA
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First protect the carboxyl group and amino group in the intermediate aspartic acid with N-hydroxysuccinimide and 2-nitrothiophenol respectively, then condense with carboxyamoxicillin, and finally hydrogenate and deprotect to obtain the product , the main disadvantage of this method in production is that 2-nitrothiophenol is used for amino protection, which is very toxic and unsafe for industrial production, and at the same time, the removal of amino protection is not complete
The yellow color produced by 2-nitrothiophenol is easy to be brought into the product, causing problems such as lower product yield and poor color formation

Method used

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  • Synthesis method of aspoxicillin

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Embodiment 1

[0032] Add D-2-amino-3-methylaminopropionic acid (100g, 0.68mol) into the three-necked flask, then add DCM and stir to dissolve under ice-water bath, then add triethylamine (103g, 1.02mol) and dicarbonate Tert-butyl ester (224g, 1.02mol). When the temperature of the reaction system dropped to 5°C, 4-dimethylaminopyridine (5g, 0.04mol) was added and reacted at this temperature for 5h. Concentrate, pour the concentrated solution into a separatory funnel, add water (2000ml), adjust PH=2 with 1mol / L HCl, extract with ethyl acetate (2000ml), wash with water 3 times (2000ml×3), saturated saline (2000ml×3), dried over anhydrous sodium sulfate, distilled off ethyl acetate under reduced pressure, added an appropriate amount of petroleum ether, stirred and crystallized at 0°C, filtered with suction, washed with a small amount of petroleum ether, and dried in vacuum. Compound 2 (163.4 g, white solid, yield 97%) was obtained.

[0033] Add compound 2 (150g, 0.60mol) and compound 3 (260g, ...

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Abstract

The invention discloses a synthesis method of aspoxicillin, belonging to the field of synthesis of chemical medicines.D-2-amino-3-methylaminopropionic acid and benzyl-protected oxyammonia penicillin used as raw materials are subjected to di-tert-butyl dicarbonate protection, esterification, deprotection and the like to synthesize the aspoxicillin. Compared with the past methods, the method disclosed by the invention has the advantages of small intermediate toxicity, fewer byproducts, fewer steps and low environmental pollution.

Description

technical field [0001] The invention relates to a method for synthesizing apoxicillin, belonging to the field of chemical drug synthesis. Background technique [0002] Apoxicillin is a β-lactam semi-synthetic antibiotic. It was first developed by Japan's Tanabe Seiyaku Company in 1987 as a new generation of broad-spectrum antibiotics. The mechanism of action of apoxicillin is to inhibit the synthesis of bacterial cell walls, causing the bacteria to absorb water and swell and die. The strength of apoxicillin against common pathogenic bacteria is 2 to 4 times that of antibiotics such as mezlocillin, azlocillin, carpicillin, and ticarcillin, and it is also better than the common cephalosporin antibiotics Ⅰ, Ⅱ, and Ⅲ. According to reports, apoxicillin with a concentration of 6.25 μg / ml can inhibit Pseudomonas aeruginosa by 88%, mezlocillin and carboxylicillin have only 18% and 12%, and ticarcillin has only 4%. %. The good curative effect of apoxicillin makes this product hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/68C07D499/04
CPCY02P20/55C07D499/68C07D499/04
Inventor 帅放文王向峰章家伟
Owner HUNAN ER KANG PHARMA
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