High performance liquid chromatography chiral separation column based on [3+3] type chiral polyamine macrocyclic compound

A technology for high performance liquid chromatography and macrocyclic compounds, which is applied in the field of high performance liquid chromatography chiral separation column and chiral separation performance, can solve the problems of complex chiral crown ether process and other problems, and achieves good chiral separation performance, heavy weight The effect of good practicability and stability, and high separation efficiency

Active Publication Date: 2022-07-01
YUNNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, crown ethers and cyclodextrins have been developed as chiral stationary phases for high performance liquid chromatography to prepare chiral columns, but they also have some shortcomings, such as the complicated process of synthesizing chiral crown ethers, and the chiral crown ether stationary phases only It has a good chiral resolution effect on amino acids and primary amine chiral compounds; chiral stationary phases such as crown ethers and cyclodextrins generally only have chiral resolution effects under reversed-phase chromatography conditions

Method used

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  • High performance liquid chromatography chiral separation column based on [3+3] type chiral polyamine macrocyclic compound
  • High performance liquid chromatography chiral separation column based on [3+3] type chiral polyamine macrocyclic compound
  • High performance liquid chromatography chiral separation column based on [3+3] type chiral polyamine macrocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of [3+3]-type chiral polyamine macrocyclic compound: Weigh 2.06g (10mmol) (1R,2R)-1,2-diphenylethylenediamine and dissolve it in 50mL of acetonitrile, 2.12g (10mmol) 2,6-Diformyl-4-tert-butylphenol was dissolved in 30 mL of acetonitrile, the two were mixed, and the reaction was stirred at room temperature for 45 minutes, and a yellow solid was precipitated in the solution. The yellow precipitate was filtered, washed with 20 mL of acetonitrile, then placed in a forced air drying oven, and dried at 60° C. for 2 hours to obtain the desired [3+3] chiral polyamine macrocyclic compound.

Embodiment 2

[0025] (1) Modified alkenyl functionalization of [3+3] type chiral polyamine macrocyclic compound: Weigh 0.7 g of [3+3] type chiral polyamine macrocyclic compound synthesized in Example 1 and dissolve it in 10 mL of anhydrous Then take 50 mL of anhydrous chloroform into another 100 mL round-bottom flask filled with nitrogen, add 0.6 g of sodium hydride, stir at 0 °C for 20 minutes, and then slowly add the above dissolved [ 3+3] chiral polyamine macrocyclic compounds in chloroform. After the dropwise addition, stirring was continued for 30 minutes, then 0.12 mL of 5-bromo-1-pentene was added, the temperature was raised to 60° C., and the mixture was stirred and refluxed for 72 hours. 20 mL of distilled water was added to separate the liquids, the organic phase was washed three times with deionized water, and then the organic phase was dried with anhydrous magnesium sulfate and then filtered with suction, and the solvent was evaporated to obtain the product.

[0026] (2) Synthe...

Embodiment 3

[0030] The chiral separation column prepared in Example 2 is in the normal phase mode, with n-hexane / isopropanol as the mobile phase, the flow rate is 0.1mL / min, the wavelength of the ultraviolet detector is 254nm, and the column temperature is 25 ℃ chromatographic conditions The separation experiment was carried out on the prepared chiral samples, and the resolution chromatograms of some chiral compounds are shown in the attached image 3 As shown, the resolved chromatographic data are listed in Table 1 below.

[0031] Table 1 Resolution results of some chiral compounds on the chiral separation column of the present invention under normal phase mode (n-hexane / isopropanol as mobile phase)

[0032]

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Abstract

The invention discloses a high performance liquid chromatography chiral separation column based on a [3 + 3] type chiral polyamine macrocyclic compound. A [3 + 3] type chiral polyamine macrocyclic compound is synthesized through condensation reaction of polyaldehyde and polyamine, the [3 + 3] type chiral polyamine macrocyclic compound is bonded to the surface of sulfydryl silica gel to serve as a high-performance liquid chromatography chiral stationary phase, and a high-pressure homogenate filling method is adopted to prepare the high-performance liquid chromatography chiral separation column. The chiral separation column has excellent chiral separation performance in a normal phase mode and a reverse phase mode, can be used for separating a plurality of chiral compounds and chiral drugs including chiral alcohol, ketone, ether, aldehyde, ester, amine and the like, has the advantages of high separation efficiency, good selectivity, simplicity in preparation, low cost, good reproducibility and stability and the like, and is suitable for industrial production. The method has a good application prospect in the field of chiral separation.

Description

technical field [0001] The invention belongs to the technical field of high-performance liquid chromatography chiral columns, in particular to a high-performance liquid chromatography prepared by a composite material formed by bonding a [3+3] type chiral polyamine macrocyclic compound on mercapto silica gel as a stationary phase Chiral separation columns and their chiral resolution performance. Background technique [0002] Chirality is very common in nature. It is like human hands. Although they are mirror-symmetrical, they cannot overlap. Many organic compounds have chirality, such as lactic acid molecules, alanine molecules and so on. Chiral compounds usually have two or more enantiomers, and different enantiomers have some differences in some properties, especially chiral drug enantiomers will show completely different biological activities in vivo and medicinal effect. In many chiral drugs, only one of its enantiomers has medicinal effects, while its other enantiomer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01D15/38B01D15/32C07F7/08C07B57/00
CPCB01D15/3833B01D15/322B01D15/325C07F7/0874C07F7/0889C07B57/00C07B2200/07C07B2200/11
Inventor 章俊辉张有萍
Owner YUNNAN NORMAL UNIV
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