Triazole singly-bonded fully-substituted cyclodextrin silica gel chiral fixed phase and preparation method thereof

A technology of chiral stationary phase and cyclodextrin, which is applied in the direction of organic chemistry methods, chemical instruments and methods, and other chemical processes, and can solve the problem that the ability of chiral resolution needs to be improved, the types of chiral resolution drugs are limited, the chiral Solve problems such as stationary phase bonding instability, achieve excellent acid-base stability and maintain chemical stability

Inactive Publication Date: 2014-09-10
NANJING XINLUOMEI NEW MATERIALS
View PDF4 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Triazole singly-bonded fully-substituted cyclodextrin silica gel chiral fixed phase and preparation method thereof
  • Triazole singly-bonded fully-substituted cyclodextrin silica gel chiral fixed phase and preparation method thereof
  • Triazole singly-bonded fully-substituted cyclodextrin silica gel chiral fixed phase and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: Taking β-cyclodextrin as an example

[0041] In conjunction with the accompanying drawings, the preparation method of the triazolyl single-bonded fully substituted-β-cyclodextrin-silica gel chiral stationary phase of the present invention comprises the following steps:

[0042] In the first step, p-toluenesulfonyl chloride and imidazole are reacted at room temperature in dichloromethane to obtain p-toluenesulfonyl imidazole;

[0043] 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;

[0044] In the third step, t...

Embodiment 2

[0076] Example 2: Taking β-cyclodextrin as an example

[0077] The method for preparing a triazolyl single-bonded permethylcyclodextrin-silica gel chiral stationary phase with broad-spectrum chiral resolution capability is characterized in that it comprises the following steps:

[0078] 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;

[0079] 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 β-cyclodextrin, 25 o After C stirred and reacted for 4 h, adding mass percent was 30% aqueous sodium hydroxide solution, filtered; adding ammonium chloride to the filtrate to adjust its pH value to 8 to obtain a white solid, filtered, precipitated and vacuum-dried to obtain the product p-toluene Sulfonyl-β-cyclodextrin;

[0080] ...

Embodiment 3

[0086] Example 3 Take α-cyclodextrin as an example

[0087] The method for preparing a triazolyl single-bonded permethylcyclodextrin-silica gel chiral stationary phase with broad-spectrum chiral resolution capability is characterized in that it comprises the following steps:

[0088] 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;

[0089] 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 α-cyclodextrin, 25 o After stirring and reacting for 4 h, add 30% sodium hydroxide aqueous solution and 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-α - Cyclodextrin, vacuum dried product;

[0090] In the third step, ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
particle diameteraaaaaaaaaa
particle diameteraaaaaaaaaa
particle diameteraaaaaaaaaa
Login to view more

Abstract

The invention discloses a method for preparing a triazolyl single-bond fully substituted cyclodextrin-silica gel chiral stationary phase through a click reaction and an application thereof. In the present invention, through the selective azidation of the 6-position of cyclodextrin, the full substitution and the alkynylation of silica gel, a newly developed catalyst is used to prepare a triazole-based single-bonded full-bonded compound with excellent chemical stability. Replacing cyclodextrin-silica gel chiral stationary phase, enriching the structure design of cyclodextrin. This type of triazolyl single-bonded fully substituted cyclodextrin chiral stationary phase exhibits excellent chiral resolution capabilities for amino acids, acidic and neutral racemic drugs in liquid chromatography, and is expected to be used as a chiral stationary phase. In the field of chiral resolution of pharmaceuticals for various chromatographic techniques.

Description

technical field [0001] The invention belongs to the field of chiral resolution of drug racemates, and successfully prepares a class of triazolyl single-bonded fully substituted cyclodextrin-silica gel chiral stationary phase, which can be applied to the chiral resolution of drugs in various chromatographic techniques Dividing and preparing. 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 ef...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/29B01J20/30C07B57/00
Inventor 吴小聪唐键唐卫华王勇
Owner NANJING XINLUOMEI NEW MATERIALS
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap