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The synthetic method of nitrocefamin

A technology of nitrocephalin and synthetic methods, applied in the direction of organic chemistry, etc., can solve the problems of unfavorable industrial production, cumbersome synthesis steps, and high price, and achieve the effects of low market price, high yield, and easy product

Inactive Publication Date: 2018-11-13
DALIAN UNIV OF TECH
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] A German patent DE 2249165 reported by the Glaxo laboratory in 1973 and an article (Synthesis 1998,145-147) in 1998 reported the synthetic method of nitrocephin, but their methods all need to first S in the raw material structure Oxidation and final reduction, the synthesis steps are cumbersome and the yield is low
In 2005, ShahriarMobashery etc. reported a new synthetic method of nitrocephin (J.Org.Chem.2005,70,367-369). The synthetic method has short steps and high yield, but the starting materials used are purchased in the market. The price is expensive, which is not conducive to industrial production

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  • The synthetic method of nitrocefamin
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  • The synthetic method of nitrocefamin

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Embodiment 1

[0055] Step 1: Add 20g of 7-ACA into a solution consisting of 140mL of methanol and 140mL of water, cool down to -10~-20°C, add 15.6mL of 10mol / L NaOH solution dropwise, stir for 10min after the dropwise addition, and maintain the temperature -10~-20°C, the reaction solution was slowly neutralized with 1mol / L HCl solution until the pH was 3, after the neutralization was completed, it was suction filtered, the filter cake was washed with methanol, acetone, ether in turn, and 14.5g was obtained after vacuum drying White 7-AHCA, the yield is 86%;

[0056] 7-AHCA 1 H NMR

[0057] 1 H NMR (400MHz, TFA) δ5.62 (d, J = 5.0Hz, 1H), 5.49 (d, J = 5.1Hz, 1H), 5.31–5.13 (m, 2H), 4.09 (d, J = 18.9Hz ,1H),3.88(d,J=19.0Hz,1H).

[0058] The second and third steps: 7.5g of 7-AHCA prepared in the first step is added to water, cooled to 0°C, and 2mol / L NaOH solution is added dropwise until 7-AHCA is completely dissolved, and the solution pH=8. Dilute 6.2g of thiopheneacetyl chloride with 14m...

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Abstract

The invention relates to a nitrocefin synthesis method and belongs to the field of drug synthesis. The invention provides a novel process for preparing nitrocefin from a compound I as a raw material. The compound I is prepared from 7-ACA. The nitrocefin synthesis method can realize synthesis of nitrocefin from 7-ACA as an initial raw material through seven processes. The 7-ACA as an initial raw material is a key intermediate of a cephalosporin, has already been industrialized and has a low market price. The nitrocefin synthesis method has the advantages of simple processes, easy reaction treatment, easy product purification, high yield, easy industrialization and low production cost.

Description

technical field [0001] The invention relates to a method for synthesizing nitrocephalin and belongs to the field of drug synthesis. Background technique [0002] Penicillins and cephalosporins are a class of antibiotics with a β-lactam structure, which are widely used in anti-infection therapy. But after long-term use of such drugs, pathogens may produce enzymes that inactivate the drugs, such as beta-lactamase. β-lactamase is a hydrolytic enzyme that can hydrolyze penicillins or cephalosporins, making antibiotics ineffective, and pathogens will develop drug resistance. Nitrocephalin is a cephalosporin, which can be used to detect whether bacteria have produced β-lactamase, that is, to detect bacterial resistance. The detection of bacterial resistance can avoid overtreatment and treatment errors as much as possible, thereby improving the efficiency and quality of treatment, reducing the pain of patients and reducing the cost of treatment. Moreover, the nitrocephalin detec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/24
CPCC07D501/24
Inventor 王保民朱国栋危倩曲景平代齐敏
Owner DALIAN UNIV OF TECH