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High performance liquid chromatography center control detection method in 7-AVCA production process

A technology of high performance liquid chromatography and 7-AVCA, applied in the field of high performance liquid chromatography detection of 7-amino-3 vinyl cephalosporanic acid, can solve the irreversible harm of liquid chromatography and chromatographic column, the inability to monitor the reaction process, the disadvantageous Industrial use and other issues, to achieve the effect of simple sample pretreatment, stable baseline and easy operation

Inactive Publication Date: 2020-12-01
河北合佳医药科技集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method can only detect the content of the generated intermediates GVNE and 7-AVCA, but it cannot monitor the reaction process and cannot distinguish the key intermediate 7-phenylacetamido-4-methoxybenzyl cephalosporanate-3- Methylene triphenylphosphine iodonium salt, 7-phenylacetamido-3-vinyl-4-cephalosporanic acid and other substances, and because the mobile phase sulfamic acid aqueous solution is too acidic (pH<1) will affect the liquid phase Chromatography and chromatographic columns cause great irreversible harm, which is not conducive to industrial use

Method used

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  • High performance liquid chromatography center control detection method in 7-AVCA production process
  • High performance liquid chromatography center control detection method in 7-AVCA production process
  • High performance liquid chromatography center control detection method in 7-AVCA production process

Examples

Experimental program
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Effect test

Embodiment 1

[0046] Take a drop of the reaction solution of GCLE's iodide and quaternary phosphine reaction product, dilute with an appropriate amount of dichloromethane, shake well, take an appropriate amount of the solution and pass it through a 0.22 μm organic microporous membrane for testing; pass the above-mentioned solution to be tested through Agilent HPLC Chromatographic analysis, column temperature 30°C, flow rate 1.0ml / min, chromatographic column: Elite C18, 250×4.6mm, 5μm chromatographic column, mobile phase ratio is A liquid: B liquid = 65:35, and the time is 40min to detect the raw material GCLE residual amount. Such as image 3 As shown by quaternary phosphine salt, 2.3min is hydrated triphenylphosphine, 4.5min is 7-phenylacetamido-4-cephalosporanic acid methoxybenzyl ester-3-methylene triphenylphosphine iodonium salt, 7.5min It is the residue of raw material GCLE, 33.5min is unreacted triphenylphosphine. Good separation.

Embodiment 2

[0048]Take the reaction solution of quaternary phosphonium salt after alkalization and Wittig reaction, dilute it with an appropriate amount of mobile phase, shake well, take an appropriate amount of the solution and pass it through a 0.22 μm organic microporous filter membrane to be tested; the above-mentioned solution to be tested is analyzed by Agilent high performance liquid chromatography , column temperature 30°C, flow rate 1.0ml / min, chromatographic column: Elite C18, 250×4.6mm, 5μm chromatographic column, mobile phase ratio is liquid A: liquid B = 65:35, time 40min to detect the quaternary phosphonium salt of the raw material residue. Such as Figure 4 As shown in the Wittig reaction, 4.5min is the unreacted residue of 7-phenylacetamido-4-cephalosporanic acid methoxybenzyl ester-3-methylenetriphenylphosphineiodonium, and 4.1min is the β-lactam ring-opening impurity , 7.4min as the main product GVNE. Good separation.

Embodiment 3

[0050] Take an appropriate amount of GVNE one-step hydrolysis reaction solution, dilute it with an appropriate amount of mobile phase, shake well, take an appropriate amount of the solution and pass it through a 0.22 μm organic microporous membrane for testing; the above-mentioned solution to be tested is analyzed by Agilent high performance liquid chromatography, the column temperature is 30 °C , flow rate 1.0ml / min, chromatographic column: Elite C18, 250×4.6mm, 5μm chromatographic column, mobile phase ratio of liquid A: liquid B = 65:35, time 40min, detect the residual amount of GVNE. Such as Figure 5 As shown in one-step hydrolysis, 2.4min is the primary hydrolysis product 7-phenylacetamido-3-vinyl-4-cephalosporanic acid, 3.5min is phenol, 3.2min is a small amount of p-methoxybenzyl alcohol that has not reacted with phenol, and 5.5 min, 6.2min and 11.0min are the ortho-pair products of hydrolyzed p-methoxybenzyl alcohol and phenol, and 7.4min is unreacted GVNE. Good separ...

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Abstract

The invention discloses a high performance liquid chromatography center control detection method in a 7-AVCA production process, and belongs to the technical field of chemical analysis and detection.A mobile phase, namely, a liquid A, is acetonitrile; a mobile phase, namely a liquid B, is an NH4H2PO4 buffer solution; the column temperature is 30-40 DEG C; the sample size is 10 [mu] L; the flow rate is 0.9 mL / min to 1.3 mL / min; the wavelength of a detector is 254nm; and the time is 40 minutes. Dichloromethane, the NH4H2PO4 buffer solution or the mobile phase are added so as to dissolve and dilute the to-be-detected sample. A reference substance solution is prepared. Detection is performed by using the high performance liquid chromatography to determine a peak position. The to-be-detected sample is detected under the same chromatographic conditions to obtain the purity of the to-be-detected sample. The high performance liquid chromatography central control detection method in the 7-AVCAindustrial synthesis process is simple, efficient, low in cost and easy to use, and can achieve efficient detection of raw materials and intermediate products.

Description

technical field [0001] The invention relates to a high performance liquid chromatography detection method for 7-amino-3 vinyl cephalosporanic acid, belonging to the technical field of chemical analysis and detection. Background technique [0002] 7-Amino-3-vinyl cephalosporanic acid (7-AVCA) Chemical name: 7-amino-3-vinyl-3-cephine-4-carboxylic acid, 7-amino-3-vinyl-8-oxygen Dai-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid or 7-AVCA; 7-amino-3-vinyl-8-oxo-5-thia -1-Azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid, English name: 7-Amino-3-vinyl-3-cephem-4-carboxylic acid; (6R,7R)-7 -ammonio-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-7-Amino-3-ethenyl-8-oxo -5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is a key intermediate for the synthesis of the third-generation cephalosporins Cefixime and Cefdinir, both of which are for oral use Cephalosporin antibiotics have strong antibacterial activity and a wide range of antibacterial ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/02G01N30/74G01N30/06G01N30/34G01N30/86G01N30/88G01N30/14
CPCG01N30/02G01N30/74G01N30/06G01N30/34G01N30/8634G01N30/88G01N30/14G01N2030/884G01N2030/146
Inventor 刘振强徐鑫林姜鹏鹏梁丙辰孙美婷刘东娜王宇栋刘新元
Owner 河北合佳医药科技集团股份有限公司
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