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

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

Inactive Publication Date: 2012-03-28
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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  • 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

[0041] Example 1: Taking β-cyclodextrin as an example

[0042] 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:

[0043] In the first step, p-toluenesulfonyl chloride and imidazole are reacted at room temperature in dichloromethane to obtain p-toluenesulfonyl imidazole;

[0044] 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;

[0045] In the third step, t...

Embodiment 2

[0077] Example 2: Taking β-cyclodextrin as an example

[0078] 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:

[0079] 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;

[0080] 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;

[0081] ...

Embodiment 3

[0087] Example 3 Take α-cyclodextrin as an example

[0088] 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:

[0089] 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;

[0090] 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;

[0091] In the third step, ...

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Abstract

The invention discloses a click reaction based preparation method and use of a triazole singly-bonded fully-substituted cyclodextrin silica gel chiral fixed phase. In the method, the triazole singly-bonded fully-substituted cyclodextrin silica gel chiral fixed phase with high chemical stability is prepared by the selective azidation of the position 6 of cyclodextrin and full substitution and alkynylation of silica gel, by using a newly developed catalyst and by a click reaction, and the structural design of cyclodextrin is enriched. The triazole singly-bonded fully-substituted cyclodextrin silica gel chiral fixed phase demonstrates high chiral resolution capacity for amino acid and acidic and neutral racemate medicines and is expected to be used in field of medicine chiral resolution of various chromatographic techniques as a chiral fixed phase.

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

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29B01J20/30C07B57/00
Inventor 吴小聪唐键唐卫华王勇
Owner NANJING XINLUOMEI NEW MATERIALS
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