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Pyridinedicarboxamido bridged bis-β-cyclodextrin stationary phase and its preparation method and application

A pyridine dicarboxamido bridge and dicarboxamido bridge technology, applied in the field of chiral separation materials, can solve problems such as difficult separation of large-volume enantiomers, and achieve stable chromatographic performance, good reproducibility, and simple process Effect

Active Publication Date: 2022-07-12
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The purpose of the present invention is to solve the above-mentioned deficiency of the performance of the derivatized cyclodextrin stationary phase, and to provide a pyridine dicarboxamido bridged double β-cyclodextrin stationary phase and a preparation method thereof, which is simple in operation and high in yield. Moreover, the prepared PyCDP can separate triazoles, flavanones and other chiral substances well under different modes such as reversed-phase chromatography and polar organic, and it is expected to solve the above-mentioned monocyclodextrin derivatives to a certain extent. It is difficult to resolve large-volume enantiomers with the fixed phase

Method used

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  • Pyridinedicarboxamido bridged bis-β-cyclodextrin stationary phase and its preparation method and application
  • Pyridinedicarboxamido bridged bis-β-cyclodextrin stationary phase and its preparation method and application
  • Pyridinedicarboxamido bridged bis-β-cyclodextrin stationary phase and its preparation method and application

Examples

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Effect test

Embodiment 1

[0029] A method for preparing a pyridine-2,3-dicarboxamido bridged bis-β-cyclodextrin stationary phase, comprising the following steps:

[0030] (1) Add mono-6-amino-β-cyclodextrin, pyridine-2,3-dicarboxylic acid, DCC, HOBT, anhydrous DMF in proportions of 6.5g, 0.25g, 0.86g, 0.54g, 30mL, Stir to dissolve, magnetic stirring reaction at room temperature for 36h. The unreacted solid was filtered, the filtrate was poured into 500 mL of acetone (calculated by the amount of 0.86 g of DCC, the same below), the precipitate was precipitated and filtered to obtain a solid crude product. The solid was dissolved in a small amount of water, purified by Sephadex (C-25) flash column, the filtrate was collected and concentrated, then acetone was added to separate out the precipitate, suction filtered, and the solid was dried under vacuum at 55 °C to obtain pyridine-2,3- Dicarboxamido-bridged bis-β-cyclodextrin (PyCD) for use as a chiral ligand;

[0031] (2) PyCD, anhydrous DMF, and 3-isocy...

Embodiment 2

[0036] A method for preparing a pyridine-2,3-dicarboxamido bridged bis-β-cyclodextrin stationary phase, comprising the following steps:

[0037] (1) Add mono-6-amino-β-cyclodextrin, pyridine-2,3-dicarboxylic acid, DCC, HOBT, anhydrous DMF in proportions of 7.0g, 0.25g, 0.86g, 0.54g, and 30mL, Stir to dissolve, magnetic stirring reaction at room temperature for 36h. The unreacted solid was filtered, the filtrate was poured into 500 mL of acetone (calculated by the amount of 0.86 g of DCC, the same below), the precipitate was precipitated and filtered to obtain a solid crude product. The solid was dissolved in a small amount of water, purified by Sephadex (C-25) flash column, the filtrate was collected and concentrated, then acetone was added to precipitate the precipitate, suction filtered, and the solid was dried under vacuum at 55 °C to obtain PyCD, which was used as a chiral compound. body;

[0038] (2) PyCD, anhydrous DMF, and 3-isocyanatopropyltriethoxysilane were added ...

Embodiment 3

[0044] A method for preparing a pyridine-2,3-dicarboxamido bridged bis-β-cyclodextrin stationary phase, comprising the following steps:

[0045] (1) Add mono-6-amino-β-cyclodextrin, pyridine-2,3-dicarboxylic acid, DCC, HOBT, anhydrous DMF in proportions of 7.5g, 0.25g, 0.86g, 0.54g, 30mL, Stir to dissolve, magnetic stirring reaction at room temperature for 36h. The unreacted solid was filtered, the filtrate was poured into 500 mL of acetone (calculated by the amount of 0.86 g of DCC, the same below), the precipitate was precipitated and filtered to obtain a solid crude product. The solid was dissolved in a small amount of water, purified by Sephadex (C-25) flash column, the filtrate was collected and concentrated, then acetone was added to precipitate the precipitate, suction filtered, and the solid was dried under vacuum at 55 °C to obtain PyCD, which was used as a chiral compound. body;

[0046] (2) PyCD, anhydrous DMF, and 3-isocyanatopropyltriethoxysilane were added in p...

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Abstract

The invention discloses a pyridinedicarboxamide group bridged bis-β-cyclodextrin stationary phase and a preparation method and application thereof. 3-Isocyanatopropyltriethoxysilane and SBA-15 are prepared as raw materials, and the preparation method has simple process, mild conditions and low cost; The stationary phase is a kind of multi-mode stationary phase with a wide range of separation objects, which can efficiently and quickly resolve a series of acidic, basic, neutral and amphoteric chiral drugs or pesticides in liquid chromatography.

Description

technical field [0001] The invention belongs to the field of chiral separation materials, and in particular relates to a pyridinedicarboxamide-based bridged bis-β-cyclodextrin stationary phase and a preparation method and application thereof. Background technique [0002] With the in-depth study of stereochemistry, the differences in enantiomeric functions of chiral compounds have increasingly attracted widespread attention from the international community. Because the spatial structure of chiral drugs can better match the chiral living substances (such as proteins, nucleic acids, biological enzymes and active polysaccharides, etc.), and has the advantages of clear target, high drug efficacy, and good curative effect, it is widely used in clinical practice. treat. But chiral drugs L- and D-isomer usually have only one kind of high activity, and the other one is not only low in activity, but also may produce toxic side effects. For example, L-dopa can be used to treat Parki...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/29B01J20/30B01D15/38
CPCB01J20/29B01J20/3078B01J20/3071B01J20/3085B01D15/3833
Inventor 李来生钟慧曾庆丽张天赐双亚洲李良
Owner NANCHANG UNIV
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