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Teicoplanin p-chlorophenyl isocyanate chiral stationary phase filling and method for preparing same

A technology of chlorophenylisocyanate and chiral stationary phase, applied in the field of analytical chemistry

Inactive Publication Date: 2007-07-11
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The p-chlorophenylisocyanate derivatives of teicoplanin chiral stationary phase are used as chiral selective agents for chromatographic separation, but there is no report at home and abroad

Method used

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  • Teicoplanin p-chlorophenyl isocyanate chiral stationary phase filling and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1) Silanization of carrier silica gel

[0035] Weigh 10 grams of Kromasil spherical silica gel carrier (particle size 5 μm, pore size 10 nm) with 3 mol L -1 After hydrochloric acid was refluxed for 4 hours, it was washed with water to neutrality, dried in vacuum, and 10ml of 3-aminopropyltriethoxysilane was added with anhydrous toluene as a solvent, then refluxed for 8 hours, cooled to room temperature, filtered, washed with toluene and methanol, Vacuum drying to obtain 3-aminopropyl silica gel;

[0036] 2) Synthesis of bonded chiral stationary phase

[0037] Take 3 grams of the above dried 3-aminopropyl silica gel, add it to anhydrous toluene, add 2ml of 1,6-diisocyanate n-hexane dropwise under ice bath and nitrogen protection, heat the mixture to 65°C for 2 hours, and cool to After room temperature, remove the solvent and 1,6-diisocyanate n-hexane, add 100ml of anhydrous pyridine solution containing 1g of teicoplanin, stir and react at 65°C for 10 hours under nitrog...

Embodiment 2

[0039] 1) Silanization of carrier silica gel

[0040]Weigh 10 grams of Lichrosorb amorphous silica gel carrier (particle size 5 μm, pore size 10 nm) with 5 mol L -1 Hydrochloric acid was refluxed for 6 hours, washed with water until neutral, dried in vacuum, using anhydrous toluene as solvent, added 3-aminopropyltriethoxysilane, refluxed for 10 hours, cooled to room temperature, filtered, washed with toluene and methanol, and dried in vacuum Get 3-aminopropyl silica gel;

[0041] 2) Synthesis of bonded chiral stationary phase

[0042] Take 3 grams of the above-mentioned dry 3-aminopropyl silica gel, add it to anhydrous toluene, add 3ml of 1,6-diisocyanate n-hexane dropwise under ice bath and nitrogen protection, heat the mixture to 70°C for 3 hours, and cool to Remove the solvent and 1,6-diisocyanate n-hexane after room temperature, add 100ml of anhydrous pyridine solution containing 2g of teicoplanin, stir and react at 70°C for 10 hours under nitrogen protection, filter, wa...

Embodiment 3

[0044] 1) Silanization of carrier silica gel

[0045] Weigh 10 grams of Lichrospher spherical silica gel carrier (particle size 5 μm, pore size 10 nm) with 5 mol L -1 Hydrochloric acid was refluxed for 4 hours, washed with water until neutral, dried in vacuo, using anhydrous toluene as solvent, added 3-aminopropyltriethoxysilane, refluxed for 8 hours, cooled to room temperature, filtered, washed with toluene and methanol, and dried in vacuo Get 3-aminopropyl silica gel;

[0046] 2) Synthesis of bonded chiral stationary phase

[0047] Take 3 grams of the above dried 3-aminopropyl silica gel, add it to anhydrous toluene, add 4ml of 1,6-diisocyanate n-hexane dropwise under ice bath and nitrogen protection, heat the mixture to 75°C for 3 hours, cool to After room temperature, remove the solvent and 1,6-diisocyanate n-hexane, add 100ml of anhydrous pyridine solution containing 2g of teicoplanin, stir and react at 75°C for 12 hours under nitrogen protection, filter, wash with pyri...

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Abstract

The invention relates to a carbanilate group carbanilate group chirality fixed phase stuff and relative production, wherein it uses silica gel as carrier; the carrier and 3-propyl triethoxysilicane to process silanization reaction; activates the carrier and distant arm; bonds silica carrier and peptide macrocyclic antibiotics, processes derivation with carbanilate group. The inventive fixed phase stuff has high chirality recognize ability and high stability to be used in any spectrum conditions. The invention can separate glutacid in reverse flow phase, to separate the salbutamolum in polar flow phase.

Description

technical field [0001] The invention relates to a teicoplanin p-chlorophenyl isocyanate chiral stationary phase filler and a preparation method thereof, belonging to the field of analytical chemistry. Background technique [0002] Chirality is one of the essential attributes of nature on which human beings depend. Biomacromolecules such as proteins, polysaccharides, and nucleic acids all have chirality. Optically active chiral substances widely exist in animals and plants. This biological stereoselectivity and stereosynthesis of optically active substances are unique instincts of biological systems. Two chiral compounds that are enantiomers often have large differences in biological activity, pharmacokinetics, and potential side effects of drugs. About half of the western medicines currently on the market contain chiral centers. About half of them are sold in the form of racemates. For this reason, the health management departments of the United States, the European Communi...

Claims

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Application Information

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IPC IPC(8): B01J20/29
Inventor 沈报春徐秀珠
Owner ZHEJIANG UNIV
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