Click preparation and application of allyl cationic cyclodextrin chiral resolution material

A technology of chiral resolution and allyl cation, applied in separation methods, solid adsorbent liquid separation, other chemical processes, etc., can solve the problem of difficulty in ensuring the stability of chromatographic separation conditions and finding multiple chiral recognition sites Bonding arms and other problems, to achieve excellent splitting ability, reduce the difficulty of immobilization, and mild reaction conditions

Inactive Publication Date: 2016-03-30
TIANJIN UNIV
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  • Summary
  • Abstract
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Problems solved by technology

[0006] In summary, the cyclodextrin chiral stationary phase has made great progress in the development of bonded arms and the synthesis of new modified cyclodextrins, but there are still some shortcomings: with the deepening of research, the immobilization The separation performance of the phase puts forward higher requirements, it is difficult to find functionalized bonding arms with multiple chiral recognition sites, and it is difficult to ensure the stability of different chromatographic separation conditions; for different modified cyclodextrin hand The neutral stationary phase can only resolve specific enantiomers, which is highly targeted

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  • Click preparation and application of allyl cationic cyclodextrin chiral resolution material
  • Click preparation and application of allyl cationic cyclodextrin chiral resolution material
  • Click preparation and application of allyl cationic cyclodextrin chiral resolution material

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preparation example Construction

[0031] Such as figure 1 Shown in the present invention, the click preparation method of allyl cationic cyclodextrin chiral resolution material, the steps are as follows:

[0032] Step 1, the preparation of mono-6-(1-allylimidazole) cyclodextrin:

[0033]Add mono-6-p-toluenesulfonyl cyclodextrin and 1-allylimidazole in an organic solvent, and the organic solution used is toluene, ethanol, acetonitrile, pyridine, N,N-dimethylformamide (DMF ), one of dimethyl sulfoxide. The mono-6-p-toluenesulfonyl cyclodextrins used were mono-6-p-toluenesulfonyl-α-cyclodextrin, mono-6-p-toluenesulfonyl-β-cyclodextrin and One of the mono-6-p-toluenesulfonyl-γ-cyclodextrins. The molar ratio of the mono-6-p-methylbenzenesulfonyl cyclodextrin to 1-allylimidazole is 1:2 to 1:5, react at 50 to 150°C for 20 to 40 hours, and then the reaction system Pour into acetonitrile to precipitate a solid, wash twice with acetonitrile, and dry to obtain mono-6-(1-allylimidazole) cyclodextrin.

[0034] The str...

Embodiment 1

[0050] 5 g of mono-6-p-toluenesulfonyl-β-cyclodextrin, 20 mL of DMF and 2 mL of 1-allylimidazole were successively added into a 100 mL three-necked flask, and the reaction was stirred at 90° C. for 36 hours. Acetonitrile was added, and a large amount of white solid was precipitated, which was filtered by suction and dried in vacuum at 60° C. for 3 hours. Mono-6-(1-allylimidazole)-β-cyclodextrin was obtained.

[0051] Dissolve mono-6-(1-allylimidazolium)-β-cyclodextrin in a 300mL beaker, install the chloride-type anion resin in an ion-exchange column, and wash it with water continuously until the resin is neutral. The mono-6-(1-allylimidazole)-β-cyclodextrin solution was poured into an ion exchange column, rinsed continuously with a large amount of water, and the obtained filtrate was spin-dried with a rotary evaporator to obtain the product.

[0052] Add 2.94g silica gel, 30mL anhydrous toluene (CaH 2 dry), 0.75mL (3-mercaptopropyl)trimethoxysilane, reflux at 120°C for 8 hou...

Embodiment 2

[0057] Add 10.5g of mono-6-p-toluenesulfonyl-β-cyclodextrin, 15mL of DMF and 3.5mL of 1-allylimidazole into a 250mL three-necked flask in sequence, and stir at 80°C for 24 hours. Acetonitrile was added, and a large amount of white solid was precipitated, which was filtered by suction and dried in vacuum at 60° C. for 3 hours. Mono-6-(1-allylimidazole)-β-cyclodextrin was obtained.

[0058] Dissolve mono-6-(1-allylimidazole)-β-cyclodextrin in a 100mL beaker, install the nitrate anion resin in an ion exchange column, and wash it with water continuously until the resin is neutral. The mono-6-(1-allylimidazole)-β-cyclodextrin solution was poured into an ion exchange column, rinsed continuously with a large amount of water, and the obtained filtrate was spin-dried with a rotary evaporator to obtain the product.

[0059] Add 2.94g of microspherical silica gel, 30mL of anhydrous toluene (CaH 2 dry), 0.75mL (3-mercaptopropyl)trimethoxysilane, reflux at 120°C for 8 hours. Filter, was...

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Abstract

The invention discloses a click preparation method of an allyl cationic cyclodextrin chiral resolution material. The click preparation method comprises following steps: preparation of mono-6-(1-allylimidazole)-cyclodextrin; ion exchange of mono-6-(1-allylimidazole)-cyclodextrin; synthesis of mercapto-silica gel; click chemical reaction for preparation of an allyl cationic cyclodextrin chiral chromatographic separation material. Through the efficient thiol-ene click chemical reaction, mono-6-(1-allylimidazole) cyclodextrin is grafted to the mercapto modified porous silica gel surface, the novel natural allyl cationic cyclodextrin chiral chromatographic separation material is prepared, and an highly universal and effective path is provided for preparation of the chiral resolution material with a stable and controllable structure. The prepared allyl cationic cyclodextrin chiral resolution material can be used for chiral separation of compounds in a reverse chromatography mode, and the separation material has excellent separation capacity for different categories of drugs such as isoxazoline, flavanone, bendroflumethiazide, 4-chromanol and the like.

Description

technical field [0001] The invention belongs to the field of chiral resolution of drug racemates, and relates to chromatographic chiral resolution materials: by grafting mono-6-(1-allylimidazole) cyclodextrin to the surface of porous silica gel modified by mercapto groups, A novel natural cationic cyclodextrin chiral chromatographic separation material was prepared. The separation material can be used for chiral resolution and preparation of medicines in various chromatographic techniques. Background technique [0002] For compounds with chiral activity, such as most drugs, their pharmacological and toxicological activities are closely related to the chiral matching between macromolecules in vivo. Therefore, there are often significant differences in the metabolism and pharmacological effects of chiral enantiomers in vivo. At first, drugs were mainly sold in the form of racemates, but later researchers discovered that one enantiomer in chiral drugs has medicinal effects, w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29B01J20/30B01D15/38
Inventor 王勇李晓旋张蕾
Owner TIANJIN UNIV
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