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Analysis method of 4-[[(4-fluorophenyl)imine]methyl]-phenol, the key intermediate of ezetimibe

An analysis method, ezetimibe technology, applied in the field of analysis, can solve the problems of non-popularity of nuclear magnetic resonance, no report of compound analysis methods, and low accuracy

Active Publication Date: 2018-02-06
REGENEX PHARMA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The existing 4-[[(4-fluorophenyl)imine]methyl]-phenol purity detection method is the nuclear magnetic resonance method with internal standard (the internal control method of Anrun Pharmaceutical Technology Co., Ltd.). Differential detection, low accuracy, and the use of nuclear magnetic resonance instruments is not yet popular, and the method is cumbersome to operate
At present, there is no analysis method report for this compound in the open literature both at home and abroad.

Method used

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  • Analysis method of 4-[[(4-fluorophenyl)imine]methyl]-phenol, the key intermediate of ezetimibe
  • Analysis method of 4-[[(4-fluorophenyl)imine]methyl]-phenol, the key intermediate of ezetimibe
  • Analysis method of 4-[[(4-fluorophenyl)imine]methyl]-phenol, the key intermediate of ezetimibe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Instruments and Conditions

[0023] Instrument: Shimadzu LC-20A high performance liquid chromatograph, electronic analytical balance

[0024] Chromatographic column: Daice lChiralpak IC columns 150 x 4.6mm, 5μm

[0025] Column temperature: 35°C

[0026] UV detection wavelength: 284nm

[0027] Mobile phase: n-hexane: isopropanol 98:2

[0028] Flow rate: 1.0ml / min

[0029] experiment procedure

[0030] Prepare impurity reference substance stock solution: take about 10 mg of each of p-fluoroaniline, p-hydroxyformaldehyde, defluorinated, defluorinated, and meta-fluorinated impurities, put them in a 100ml volumetric flask, dissolve them with isopropanol: n-hexane (10:90) and Dilute to the mark, shake well, and get it;

[0031] Prepare the impurity reference substance solution: accurately pipette 1.0ml of the reference substance stock solution, put it in a 10ml volumetric flask, dissolve in isopropanol:n-hexane (10:90) and dilute to the mark, shake well, and you get it;...

Embodiment 2

[0039] Instruments and Conditions

[0040] Instrument: Shimadzu LC-20A high performance liquid chromatograph, electronic analytical balance

[0041] Chromatographic column: Daicel Chiralpak IC columns 250 x 4.6mm, 5μm

[0042] Column temperature: 20°C

[0043] UV detection wavelength: 284nm

[0044] Mobile phase: n-hexane: isopropanol 96:4

[0045] Flow rate: 1.0ml / min

[0046] experiment procedure

[0047] Take 10 μl of the 4-[[(4-fluorophenyl)imine]methyl]-phenol mixed solution prepared in Example 1, perform HPLC analysis according to the above conditions, and record the chromatogram.

[0048] test results

[0049]

[0050] Conclusion: 4-[[(4-fluorophenyl)imine]methyl]-phenol can be baseline separated from each impurity to be detected and each impurity to be detected.

Embodiment 3

[0052] Instruments and Conditions

[0053] Instrument: Shimadzu LC-20A high performance liquid chromatograph, electronic analytical balance

[0054] Chromatographic column: Daicel Chiralpak IC columns 150 x 2.1mm, 5μm

[0055] Column temperature: 40°C

[0056] UV detection wavelength: 275nm

[0057] Mobile phase: n-hexane: isopropanol 99:1

[0058] Flow rate: 0.5ml / min

[0059] experiment procedure

[0060] Take 10 μl of the 4-[[(4-fluorophenyl)imine]methyl]-phenol mixed solution prepared in Example 1, perform HPLC analysis according to the above conditions, and record the chromatogram.

[0061] test results

[0062]

[0063] Conclusion: 4-[[(4-fluorophenyl)imine]methyl]-phenol can be baseline separated from each impurity to be detected and each impurity to be detected.

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Abstract

The invention discloses a method for analyzing and detecting 4-[[(4-fluorophenyl)imine]methyl]-phenol, a key intermediate of ezetimibe, and its application. The method uses silica gel to bond cellulose- The tris(3,5-dichlorophenylcarbamate) chiral column can analyze and detect 4-[[(4-fluorophenyl)imine]methyl]-phenol, which can monitor the focus of the target well Impurities: chlorinated impurities, defluorinated impurities and meta-fluorine impurities, and the operation is simple and convenient, with strong specificity, suitable for daily application of 4-[[(4-fluorophenyl)imine]methyl]-phenol related substances and Content testing.

Description

technical field [0001] The invention belongs to the technical field of analysis, and in particular relates to an analysis and detection method of 4-[[(4-fluorophenyl)imine]methyl]-phenol, a key intermediate of ezetimibe, and an application thereof. Background technique [0002] 4-[[(4-fluorophenyl)imine]methyl]-phenol is the key intermediate in the synthesis of ezetimibe, which is a selective cholesterol absorption inhibitor and has been widely used clinically. The three impurities contained in 4-[[(4-fluorophenyl)imine]methyl]-phenol-chlorinated impurities, defluorinated impurities and meta-fluorine impurities will participate in the reaction and be carried to the final product, affecting the purity of the final product and yield, so the above-mentioned impurities are preferably controlled in the starting material. [0003] 4-[[(4-fluorophenyl)imine]methyl]-phenol, CAS: 3382-63-6 [0004] Chlorinated impurities Defluorinated impurities Fluorine impurity [0005] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N30/02
Inventor 卢生杰陈敏高曙光汤丹袁永玲左联卢智俊
Owner REGENEX PHARMA LTD
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