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A method for analyzing and separating cis-bicyclo[3,2,0]hept-2-en-6-one enantiomers by HPLC

A technique for analyzing and separating enantiomers, which is applied in the field of chromatographic analysis, can solve problems such as few reports of enantiomers, achieve the effects of improving drug quality, avoiding interference, and ensuring medication safety

Active Publication Date: 2018-02-06
CHANGCHUN BC&HC PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In recent years, with the diversification of chiral chromatographic packing materials, the application of chiral chromatographic column liquid chromatography has become more and more extensive. However, the use of chiral chromatographic column high performance liquid Enantiomers of en-6-ones are rarely reported

Method used

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  • A method for analyzing and separating cis-bicyclo[3,2,0]hept-2-en-6-one enantiomers by HPLC

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Instruments and Conditions

[0033] Chromatographic column: Chiralpak AD-H (250×4.6mm, 5.0μm);

[0034] Mobile phase: n-hexane-isopropanol (87:13);

[0035] Column temperature: 50°C;

[0036] Flow rate: 0.4mL / min;

[0037] Injection volume: 1μL;

[0038] Detection wavelength: 205nm;

[0039] Experimental procedure

[0040] Precisely measure 100 μL of cis-bicyclo[3,2,0]hept-2-en-6-one enantiomer, put it in a 10mL volumetric flask, dissolve and dilute with n-hexane-isopropanol (87:13) To the mark, shake well, as the test solution. Draw 1 μL of the test solution into the liquid chromatography, the column temperature is 50°C, the flow rate is 0.4mL / min, and the chromatogram is recorded.

[0041] Experimental results: (1R,5S)-bicyclo[3,2,0]hept-2-en-6-one and (1S,5R)-bicyclo[3,2,0]hept-2-en-6-one The degree of separation of the two enantiomers was 3.9, and the cis-bicyclo[3,2,0]hept-2-en-6-one enantiomer could be completely separated.

Embodiment 2

[0043] Instruments and Conditions

[0044] Chromatographic column: Chiralpak AD-H (250×4.6mm, 5.0μm);

[0045] Mobile phase: n-hexane-isopropanol (99:1);

[0046] Column temperature: 14°C;

[0047] Flow rate: 0.5mL / min;

[0048] Injection volume: 20μL;

[0049] Detection wavelength: 220nm;

[0050] Experimental procedure

[0051]Precisely measure 10 μL of cis-bicyclo[3,2,0]hept-2-en-6-one enantiomer, put it in a 10mL volumetric flask, dissolve and dilute with n-hexane-isopropanol (99:1) To the mark, shake well, as the test solution. Draw 20 μL of the test solution into the liquid chromatography, the column temperature is 14°C, the flow rate is 0.5mL / min, and the chromatogram is recorded.

[0052] Experimental results: (1R,5S)-bicyclo[3,2,0]hept-2-en-6-one and (1S,5R)-bicyclo[3,2,0]hept-2-en-6-one The resolution of the two enantiomers was 4.8, and the cis-bicyclo[3,2,0]hept-2-en-6-one enantiomer could be completely separated.

Embodiment 3

[0054] Instruments and Conditions

[0055] Chromatographic column: Chiralpak AD-H (250×4.6mm, 5.0μm);

[0056] Mobile phase: n-hexane-isopropanol (90:10);

[0057] Column temperature: 18°C;

[0058] Flow rate: 0.5mL / min;

[0059] Injection volume: 5μL;

[0060] Detection wavelength: 215nm;

[0061] Experimental procedure

[0062] Precisely measure 50 μL of cis-bicyclo[3,2,0]hept-2-en-6-one enantiomer, put it in a 10 mL volumetric flask, dissolve and dilute with n-hexane-isopropanol (90:10) To the mark, shake well, as the test solution. Draw 5 μL of the test solution into the liquid chromatography, the column temperature is 18°C, the flow rate is 0.5mL / min, and the chromatogram is recorded.

[0063] Experimental results: (1R,5S)-bicyclo[3,2,0]hept-2-en-6-one and (1S,5R)-bicyclo[3,2,0]hept-2-en-6-one The degree of separation between the two enantiomers was 4.1. The cis-bicyclo[3,2,0]hept-2-en-6-one enantiomer could be completely separated.

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Abstract

The invention discloses a method for analyzing and separating a cis-bicyclo[3,2,0]hept-2-ene-6-one enantiomer by HPLC (High Performance Liquid Chromatography). By adopting the HPLC method in which a chiral HPLC column takes a normal phase mixed solvent as a mobile phase, the cis-bicyclo[3,2,0]hept-2-ene-6-one enantiomer can be effectively analyzed and separated. The chiral HPLC column is a polysaccharide derivative normal phase coating type chiral HPLC column; the surface of silica gel is coated with amylose-tris(3,5-dimethylphenylcarbamate) or amylose-tris[(S)-alpha-methylphenylcarbamate]. The mobile phase used by normal phase chromatography is a normal hexane and isopropanol mixing solvent or a normal hexane and absolute ethyl alcohol mixing solvent. The analyzing and separating method disclosed by the invention is simple, quick, accurate and efficient, and can be used for preparing high-purity cis-bicyclo[3,2,0]hept-2-ene-6-one enantiomer; by using the analyzing and separating method, the quality controllability of the cis-bicyclo[3,2,0]hept-2-ene-6-one enantiomer can be guaranteed.

Description

technical field [0001] The invention relates to a chromatographic analysis method, in particular to a high-performance liquid chromatography method for analyzing and separating cis-bicyclo[3,2,0]hept-2-en-6-one enantiomers. technical background [0002] Prostaglandins are an important class of endogenous physiologically active substances, which regulate various physiological functions of the human body at the level of hormone concentration, and have regulatory effects on blood pressure, smooth muscle contraction, gastric juice secretion and platelet aggregation. Prostaglandins are trace components that widely exist in human and animal tissues, and the content is extremely low. Natural sources of prostaglandins cannot meet the needs of clinical medication. For this reason, the research on the total synthesis of prostaglandin derivatives is very important. [0003] Cis-bicyclo[3,2,0]hept-2-en-6-one is an important intermediate in the synthesis of prostaglandin drugs, and its ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N30/02
CPCG01N30/02G01N2030/027
Inventor 王淑红修志明李臣赵春影谢晓娜
Owner CHANGCHUN BC&HC PHARMA TECH CO LTD
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