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HPLC (High Performance Liquid Chromatography) method for analytical separation of cis-2-oxabicyclo[3,3,0]octyl-6-en-3-one enantiomer

A technology of enantiomers and oxabicycles, applied in material separation, analysis materials, measuring devices, etc., can solve the problems of cis 2-oxabicycles, etc., to ensure stability and improve drug quality , to ensure the effect of drug safety

Inactive Publication Date: 2016-10-12
CHANGCHUN BC&HC PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the analysis and separation of enantiomers containing chiral carbon atoms has always been a key issue in the synthesis and quality control of chiral drugs. After searching the literature, no cis-2-oxabicyclo[3,3,0 ]Related reports on detection methods of oct-6-en-3-one enantiomers

Method used

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  • HPLC (High Performance Liquid Chromatography) method for analytical separation of cis-2-oxabicyclo[3,3,0]octyl-6-en-3-one enantiomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Instruments and Conditions

[0025] Chromatographic column: BC chiral OD (250×4.6mm, 5.0μm)

[0026] Mobile phase: n-hexane-isopropanol (85:15)

[0027] Column temperature: 50°C

[0028] Flow rate: 0.3mL / min

[0029] Injection volume: 2μL

[0030] Detection wavelength: 200nm

[0031] Experimental procedure

[0032] Accurately measure 100 μL of cis-2-oxabicyclo[3,3,0]oct-6-en-3-one enantiomer, place it in a 10 mL volumetric flask, and mix n-hexane-isopropanol (85:15 ) was dissolved and diluted to the mark, shaken up, as the test solution. Draw 2 μL of the test solution into the liquid chromatograph, and record the chromatogram.

[0033] Experimental results: (1S,5R)-2-oxabicyclo[3,3,0]oct-6-en-3-one and (1R,5S)-2-oxabicyclo[3,3,0]octane The resolution of the two enantiomers of -6-en-3-one is 1.7, and the cis 2-oxabicyclo[3,3,0]oct-6-en-3-one enantiomer can completely separated.

Embodiment 2

[0035] Instruments and Conditions

[0036] Chromatographic column: BC chiral OD (250×4.6mm, 5.0μm)

[0037] Mobile phase: n-hexane-isopropanol (85:15)

[0038] Column temperature: 15°C

[0039] Flow rate: 0.5mL / min

[0040] Injection volume: 10μL

[0041] Detection wavelength: 205nm

[0042] Experimental procedure

[0043] Accurately measure 10 μL of cis-2-oxabicyclo[3,3,0]oct-6-en-3-one enantiomer, place it in a 10 mL volumetric flask, and mix n-hexane-isopropanol (85:15 ) was dissolved and diluted to the mark, shaken up, as the test solution. Draw 10 μL of the test solution into the liquid chromatograph, and record the chromatogram.

[0044] Experimental results: (1S,5R)-2-oxabicyclo[3,3,0]oct-6-en-3-one and (1R,5S)-2-oxabicyclo[3,3,0]octane The resolution of the two enantiomers of -6-en-3-one is 1.8, and the cis 2-oxabicyclo[3,3,0]oct-6-en-3-one enantiomer can completely separated.

Embodiment 3

[0046] Instruments and Conditions

[0047] Chromatographic column: BC chiral OD (250×4.6mm, 5.0μm)

[0048] Mobile phase: n-hexane-isopropanol (98:2)

[0049] Column temperature: 22°C

[0050] Flow rate: 1.0mL / min

[0051] Injection volume: 20μL

[0052] Detection wavelength: 205nm

[0053] Experimental procedure

[0054] Precisely measure 50 μL of cis-2-oxabicyclo[3,3,0]oct-6-en-3-one enantiomer, put it in a 10mL volumetric flask, and mix n-hexane-isopropanol (98:2 ) was dissolved and diluted to the mark, shaken up, as the test solution. Draw 20 μL of the test solution into the liquid chromatograph, and record the chromatogram.

[0055]Experimental results: (1S,5R)-2-oxabicyclo[3,3,0]oct-6-en-3-one and (1R,5S)-2-oxabicyclo[3,3,0]octane The resolution of the two enantiomers of -6-en-3-one is 1.9, and the cis 2-oxabicyclo[3,3,0]oct-6-en-3-one enantiomer can completely separated.

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Abstract

The invention discloses a method for analyzing and separating enantiomers of cis-2-oxabicyclo[3,3,0]oct-6-en-3-one. An HPLC method using a chiral chromatographic column with a positive mixed solvent as the mobile phase. The method can analyze and separate cis 2-oxabicyclo[3,3,0]oct-6-en-3-one enantiomer simply, accurately and efficiently, thereby realizing the cis-2-oxabicyclo[ Quality control of the enantiomers of 3,3,0]oct-6-en-3-one. The present invention can also be used to prepare cis-2-oxabicyclo[3,3,0]oct-6-en-3-one with high purity and single optical activity.

Description

technical field [0001] The present invention relates to a chromatographic analysis and separation method, especially a high-performance liquid chromatography method for analyzing and separating cis-2-oxabicyclo[3,3,0]oct-6-en-3-one enantiomers . technical background [0002] Prostaglandin is an active substance composed of a class of unsaturated fatty acids that exists in animals and humans and has a variety of physiological effects. The content is extremely low. Therefore, the research on the total synthesis of prostaglandin drugs is very important. cis 2-oxabicyclo[3,3,0]oct-6-en-3-one is a commonly used intermediate and starting material for the synthesis of prostaglandin drugs, and its molecular formula is C 7 h 8 o 2 , English name: cis-2-Oxabicyclo[3.3.0]Oct-6-En-3-One, the structural formula is: [0003] [0004] There are 2 chiral centers in this molecule, and there are 4 optical isomers in theory, but according to its reaction mechanism and synthesis method, ...

Claims

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Application Information

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IPC IPC(8): G01N30/02
CPCG01N30/02G01N2030/027
Inventor 王淑红孙中研彭悦赵春影修志明
Owner CHANGCHUN BC&HC PHARMA TECH CO LTD
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