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Lactide-derived chiral stationary phase as well as preparation method and application thereof

A technology of chiral stationary phase and lactide, which is applied in the field of high performance liquid chromatography, can solve the problems that chiral compounds cannot be separated, and achieve the effect of excellent separation performance, mild reaction conditions, and cheap and easy-to-obtain raw materials

Active Publication Date: 2021-11-16
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although many existing chiral stationary phases have wide applicability and good chiral selectivity, there are still some chiral compounds with specific structures that cannot be effectively resolved on the existing chiral stationary phases.

Method used

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  • Lactide-derived chiral stationary phase as well as preparation method and application thereof
  • Lactide-derived chiral stationary phase as well as preparation method and application thereof
  • Lactide-derived chiral stationary phase as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] A chiral stationary phase derived from lactide, the preparation method of which comprises the following steps:

[0056] 1) Add 20g of L-lactide, 29.66g of N-bromosuccinimide and 300mL of toluene into a 500mL three-necked flask with a reflux condenser, heat the mixture to reflux under mechanical stirring, and then Disperse 1.14 g of azobisisobutyronitrile with 50 mL of toluene and drop it into a three-necked flask through a dropping funnel. After the addition, stir at 80°C for 20 h, cool the reaction solution to room temperature, filter, and evaporate the filtrate to dryness. The obtained solid (light yellow) was dissolved in dichloromethane, washed 3 times with saturated sodium bisulfite solution, washed 1 time with saturated NaCl solution, and the organic layer was washed with MgSO 4 After drying and evaporating to dryness, bromolactide was obtained (white crystals, yield 53%);

[0057] 2) Add 20.5g of brominated lactide and 200mL of dichloromethane into a three-nec...

Embodiment 2

[0063] A chiral stationary phase derived from lactide, the preparation method of which comprises the following steps:

[0064] The SiO of 3.5g embodiment 1 2 -PMLA was dispersed in 30mL of anhydrous N,N-dimethylformamide (DMF), and then 18mL of (R)-(+)-1-phenylethylamine was added dropwise, and after the addition was completed, it was reacted at room temperature for 48h and filtered. The filtered solid was washed 3 times with acetonitrile, and dried under vacuum at 60°C for 15 h to obtain the lactide-derived chiral stationary phase SiO 2 -PMLA-NH 2 .

[0065] SiO 2 -PMLA-NH 2 The synthetic reaction of is as follows:

[0066]

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Abstract

The invention discloses a lactide-derived chiral stationary phase as well as a preparation method and application thereof. The structural formula of the lactide-derived chiral stationary phase is shown as a formula (I) or a formula (II), the formula (I) is SiO2-PMLA, the formula (II) is SiO2-PMLA-NH2, in the formulaS, silica gel particles are adopted, and n is an integer ranging from 50 to 200. The lactide-derived chiral stationary phase has excellent resolution performance, can resolve various different types of enantiomers under lower pressure, is quick and efficient in separation, has higher reproducibility, can be repeatedly used, and is simple in preparation process, mild in reaction condition, controllable in reaction and suitable for practical application.

Description

technical field [0001] The invention relates to the technical field of high performance liquid chromatography, in particular to a lactide-derived chiral stationary phase and a preparation method and application thereof. Background technique [0002] As we all know, the vast majority of drugs are composed of chiral molecules, and two chiral molecules may have significantly different physiological activities (eg, drug efficacy, drug toxicity, drug safety, etc.). At present, the top-selling drugs in the world are basically chiral compounds. It can be seen that chiral resolution is very important for the pharmaceutical industry. [0003] High-performance liquid chromatography (HPLC) is a commonly used chiral separation method, and it is of great significance to develop a system with high-efficiency resolution, wide applicability and high loading capacity. There are many systems with chiral resolution capabilities, including natural polymers such as proteins, crown ethers, and c...

Claims

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Application Information

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IPC IPC(8): C08G83/00C08G63/08C08G63/78B01D15/20B01J20/286
CPCC08G83/001C08G63/08C08G63/78B01J20/286B01D15/20
Inventor 裴媛媛文韬
Owner SOUTH CHINA UNIV OF TECH
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