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Aromatic amide type resin loaded with chiral helix and its preparation method and application

An aromatic amide type resin technology, applied in the field of chiral separation, can solve the problems of product loss, affecting the purity of chiral separation products, affecting the separation effect, etc., and achieve the effect of changing the retention time

Active Publication Date: 2022-04-12
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application finds that the product is used for chiral separation, and there are still many problems: (1) after the product is coated on the stationary phase, it is directly used for chiral separation, and the mobile phase will wash away the surface product, causing product loss and affecting the hand. (2) The product will dimerize to form an antiparallel double helix structure, and the cavity has no opening, so the separated substance cannot enter the cavity, which affects the separation effect

Method used

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  • Aromatic amide type resin loaded with chiral helix and its preparation method and application
  • Aromatic amide type resin loaded with chiral helix and its preparation method and application
  • Aromatic amide type resin loaded with chiral helix and its preparation method and application

Examples

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Effect test

Embodiment 1

[0041] An aromatic amide resin loaded with chiral helix is ​​prepared by the following method.

[0042] (1) reacting a compound with a three-center hydrogen bond control group with a halogen-substituted resin to generate an intermediate;

[0043] In this embodiment, the compound having a three-center hydrogen bond controlling group is compound 8, the halogen-substituted resin is compound 101, and the intermediate is compound 102.

[0044] Preparation of compound 102, prepared by the following method:

[0045] Step a: Take a 50mL two-necked bottle, add 0.55g compound 1 (1.59mmol), 0.38g compound 2 (1.59mmol), 1.66g PyBOP (3.19mmol), add 5mL anhydrous dichloromethane to dissolve the reactant under nitrogen protection , and 0.52 mL of anhydrous N,N-diisopropylethylamine (3.18 mmol) was added dropwise. After overnight reaction, the solvent was spin-dried to obtain a crude product, which was separated by column chromatography to obtain compound 3. Yield 82%.

[0046] Step b: Ta...

Embodiment 2

[0059] Compound 103 was repeated step h and step i twice to obtain compound 104.

[0060] The preparation route of embodiment 1-2 is as figure 1 shown.

Embodiment 3

[0062] The preparation route of this example is the same as that of Example 1, and the Ar in the helical cavity group containing Ar is different. In this example, the helical cavity group containing Ar is 6-amino-2-pyridinecarboxylic acid, and the final product is compound 105.

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Abstract

The invention belongs to the technical field of chiral separation, and in particular relates to an aromatic amide resin loaded with a chiral helix, a preparation method and application thereof. The invention uses a polypeptide solid-phase synthesis method to prepare a resin loaded with chiral aromatic amide oligomers. The chiral oligomer part has a pre-organized cavity structure, and the structure is stable and uniform in size. When used for chiral separation, it is beneficial to Enantiomers will enter the helical cavity or interact with the chiral helical folded body, thereby changing the retention time of different chiral isomers through the chromatographic column to achieve separation and purification.

Description

technical field [0001] The invention belongs to the technical field of chiral separation, and in particular relates to an aromatic amide resin loaded with chiral helix, a preparation method and application thereof. Background technique [0002] With the continuous development of scientific research, people will come into contact with more and more unnatural chiral compounds in daily life, such as chiral drugs, chiral pesticides and chiral chemical products. Studies have found that the enantiomers of chiral compounds have similar physical and chemical properties in the achiral environment, but their biological activities and pharmacological reactions are significantly different in the chiral environment. The correct use of chiral compounds can bring more convenience to people's lives; the wrong use of chiral compounds will bring a variety of side effects, which have a great impact on people's health, biological reproduction and ecological environment. Therefore, the developm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F8/18C08F8/30C08F212/14B01J20/29
CPCC08F8/18C08F8/30B01J20/29C08F212/14
Inventor 甘泉李绚覃天刘鑫璐李浩辰袁佳怡张博源
Owner HUAZHONG UNIV OF SCI & TECH