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Triazolyl bonded cyclodextrin-silica gel chiral stationary phase and preparation method thereof

A technology of chiral stationary phase and cyclodextrin, which is applied in chemical instruments and methods, other chemical processes, etc., can solve the problems of limited types of chiral resolution drugs, chiral stationary phase bonding instability, and chiral resolution The ability needs to be improved, etc., to achieve excellent acid-base stability, maintain chemical stability, and deterministic structure

Inactive Publication Date: 2012-02-08
NANJING XINLUOMEI NEW MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In view of the instability of the currently developed cyclodextrin chiral stationary phase bonding, the limited types of chiral resolution drugs, and the ability of chiral resolution needs to be improved

Method used

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  • Triazolyl bonded cyclodextrin-silica gel chiral stationary phase and preparation method thereof
  • Triazolyl bonded cyclodextrin-silica gel chiral stationary phase and preparation method thereof
  • Triazolyl bonded cyclodextrin-silica gel chiral stationary phase and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Taking β-cyclodextrin as an example

[0038] In conjunction with the accompanying drawings, the preparation method of the double substituted double punctual center-β-cyclodextrin of the present invention comprises the following steps:

[0039] In the first step, p-toluenesulfonyl chloride and imidazole are reacted at room temperature in dichloromethane to obtain p-toluenesulfonyl imidazole;

[0040] In the second step, the product p-toluenesulfonyl imidazole obtained in the first step is placed in the aqueous solution of dissolving β-cyclodextrin, stirred at room temperature for 2~4 h, and then sodium hydroxide solution is added, and a small amount of precipitate produced is removed by filtration Add ammonium chloride to the filtrate to adjust its pH value to 6-9 to obtain a white solid substance, filter to obtain the product p-toluenesulfonyl-β-cyclodextrin (Ts-CD), and vacuum-dry the product;

[0041] In the third step, take a double-necked round bottom fl...

Embodiment 2

[0066] Example 2 with α-cyclodextrin as an example

[0067] The method for preparing a triazolyl-bonded cyclodextrin-silica gel chiral stationary phase with broad-spectrum chiral resolution capability is characterized in that it comprises the following steps:

[0068] The first step, based on the mechanism of nucleophilic substitution, 1 mol of p-toluenesulfonyl chloride and 3 mol of imidazole in dichloromethane, 25 o C reaction obtains p-methylbenzenesulfonyl imidazole overnight;

[0069] In the second step, 2 mol of p-toluenesulfonyl imidazole, the product obtained in the first step, is placed in an aqueous solution of 1 mol α-cyclodextrin, 25 o After C stirred and reacted for 4 h, add mass percent and be 30% sodium hydroxide aqueous solution, filter; Add ammonium chloride to the filtrate to adjust its pH value to 8 to obtain a white solid substance, filter to obtain the product p-toluenesulfonyl-α - Cyclodextrin Ts-CD, vacuum dried product;

[0070] In the third step, ...

Embodiment 3

[0076] The method for preparing a triazolyl-bonded cyclodextrin-silica gel chiral stationary phase with broad-spectrum chiral resolution capability is characterized in that it comprises the following steps:

[0077] The first step, based on the mechanism of nucleophilic substitution, 1 mol of p-toluenesulfonyl chloride and 3 mol of imidazole in dichloromethane, 25 o C reaction obtains p-methylbenzenesulfonyl imidazole overnight;

[0078] In the second step, 2 mol of p-toluenesulfonyl imidazole, the product obtained in the first step, is placed in an aqueous solution of 1 mol of γ-cyclodextrin, 25 o After stirring the reaction for 4 h, add mass percent and be 30% sodium hydroxide aqueous solution, filter; add ammonium chloride to the filtrate to adjust its pH value to 8 to obtain a white solid substance, and filter to obtain the product p-toluenesulfonyl-γ - Cyclodextrin Ts-CD, vacuum dried product;

[0079] In the third step, 6-p-methylbenzenesulfonyl-γ-cyclodextrin (3.1 g, ...

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Abstract

The invention discloses a method for preparing a triazolyl bonded cyclodextrin-silica gel chiral stationary phase through a click reaction and application of the method. In the invention, through selective azidation of the 6-hydroxyl of cyclodextrin and alkynylation of silica gel, and by making use of a click reaction with a newly developed catalyst, the triazolyl bonded cyclodextrin-silica gel chiral stationary phase with excellent chemical stability is then prepared, thus enriching the structural design of cyclodextrin. The triazolyl bonded cyclodextrin-silica gel chiral stationary phase ofthe invention shows an excellent chiral separation ability to amino acid, acid and neutral racemic drugs in a liquid chromatogram, thus being expected to be applied in the field of drug chiral separation of various chromatographic techniques as a chiral stationary phase.

Description

technical field [0001] The invention belongs to the field of chiral separation of drug racemates, and successfully prepares a class of triazolyl-bonded cyclodextrin-silica gel chiral stationary phase, which can be applied to the chiral separation and separation of drugs in various chromatographic techniques. In preparation. Background technique [0002] Cyclodextrin (Cyclodextrin, CD) is composed of 7 D-glucose molecules connected by α-(1,4) glycosidic bonds, and is a cyclic oligosaccharide molecule in the shape of a circular truncated oligosaccharide. The inside of the cavity is shielded by two rings of hydrogen atoms (H-3 and H-5) and a ring of glycosidic bonded oxygen atoms under the shield of the C-H bond, so the inner cavity of the cyclodextrin is hydrophobic, and the cyclodextrin molecule The outer frame is hydrophilic due to the aggregation of hydroxyl groups. The cavity-like hydrophobic cavity based on cyclodextrin, under the influence of steric effect, becomes a s...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30
Inventor 吴小聪唐键唐卫华王勇
Owner NANJING XINLUOMEI NEW MATERIALS
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