Stable isotope labeled metronidazole and synthesis method thereof

A stable isotope and synthetic method technology, applied in the field of chemical synthesis, can solve the problems of long synthetic process route, limited application, strict experimental conditions, etc., and achieve the effects of short process route, high use value, and easy separation and purification.

Pending Publication Date: 2022-02-22
SHANGHAI ANPEL SCI INSTR
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent document CN106674123B discloses the synthesis method of metronidazole labeled with stable isotope tritium. The process route is long and the experimental conditions are strict, which limits the application

Method used

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  • Stable isotope labeled metronidazole and synthesis method thereof
  • Stable isotope labeled metronidazole and synthesis method thereof
  • Stable isotope labeled metronidazole and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis process of stable isotope-labeled metronidazole is as follows:

[0034] S1. Weigh 15g of 2-bromoethanol-D4 into a 100mL three-neck flask, place it in an oil bath, set up a cooling collection device, and place the cold trap at -78°C. Insert the nitrogen needle below the liquid level and pass nitrogen protection. Then use a constant pressure dropping funnel to slowly drop 45mL of 25% NaOH solution into the solution, and control the drop to finish in about half an hour. After the drop, the temperature was raised to 100°C and kept for half an hour. The isotope-labeled oxirane was collected in the cold trap and immediately used for subsequent synthesis.

[0035] S2, when preparing the raw material for the first step, weigh 3.3 g of the raw material imidazole, put it into the reaction tube, add 8 mL of the mixed solution of formic acid and sulfuric acid (formic acid:concentrated sulfuric acid=8:1, volume ratio), Heat to 80°C to dissolve all imidazole as a raw ...

Embodiment 2

[0039] The synthesis process of stable isotope-labeled metronidazole is as follows:

[0040] S1. Weigh 15g of 2-bromoethanol-D4 into a 100mL three-neck flask, and place it in an oil bath; set up a cooling collection device, and place the cold trap at -70°C. Insert the nitrogen needle below the liquid level and start bubbling. Then use a constant pressure dropping funnel to add 45mL of 30% NaOH solution drop by drop to the solution at 1 drop per second, and control the drop to finish in about 40min. After dripping, start to heat up to 90°C and keep it for half an hour. Isotope-labeled oxirane is collected in the cold trap and used for subsequent synthesis immediately;

[0041] S2, when preparing the raw material for the first step, weigh 3.3 g of the raw material imidazole, put it into the reaction tube, add 8 mL of the mixed solution of formic acid and sulfuric acid (formic acid:concentrated sulfuric acid=7:1, volume ratio), Heat to 80°C to dissolve all imidazole as a raw mate...

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Abstract

The invention discloses stable isotope labeled metronidazole and a synthesis method thereof. The synthesis method comprises the following steps: S1, carrying out intramolecular ring closing on stable isotope labeled bromoethanol under an alkaline condition to prepare stable isotope labeled ethylene oxide; and S2, reacting the stable isotope labeled ethylene oxide and 2-methyl-5-nitroimidazole, to obtain the stable isotope labeled metronidazole. Compared with the prior art, the synthetic process is mild in condition, simple in process and short in process route, the product is easy to separate and purify, the chemical purity and stable isotope abundance of the obtained product both reach 99% or above, and the requirements of the product as a standard reagent for quantitative detection of metronidazole are met; and the use value is high, and the economical efficiency is good.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a stable isotope-labeled metronidazole and a synthesis method thereof. Background technique [0002] Metronidazole, also known as metronidazole, belongs to the nitroimidazole class of synthetic antibacterial drugs. It is mainly used clinically to prevent and treat infections caused by anaerobic bacteria. However, studies have shown that it has potential risks of teratogenicity, carcinogenicity, mutagenesis and genotoxicity. In order to ensure food safety, many countries currently require that such drugs should not be detected in food animals, feed and related products. [0003] At present, the traditional detection methods of metronidazole residue mainly include high performance liquid chromatography, thin layer chromatography, immunoassay, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, spectrometry, voltammetry, etc. The analysis meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/94C07B59/00
CPCC07D233/94C07B59/002C07B2200/05
Inventor 朱倩陈武炼徐敏
Owner SHANGHAI ANPEL SCI INSTR
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