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Chiral MOC liquid chromatography separation column for resolution of racemic compounds

A liquid chromatography column and liquid chromatography technology, applied in the field of chiral MOC liquid chromatography column, can solve the problems of pore window size, cavity size and shape chiral recognition ability, etc., and achieve good application prospects, separation The effect is good and the raw materials are simple and easy to obtain

Active Publication Date: 2019-04-30
YUNNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since the pore window size, cavity size and shape of porous organic molecular cages affect its chiral recognition ability, it is still a big problem to construct chiral porous organic cages with stable structures.

Method used

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  • Chiral MOC liquid chromatography separation column for resolution of racemic compounds
  • Chiral MOC liquid chromatography separation column for resolution of racemic compounds
  • Chiral MOC liquid chromatography separation column for resolution of racemic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0024] Synthesis of 1,4-bis(2-imidazole formaldehyde)butane: in N 2 Under protection, add 40mL of anhydrous DMF to a 100mL round-bottomed flask, then add 2-imidazole formaldehyde (2.6906g), 1,4-dibromobutane (2.1594g) and potassium carbonate (2.7642g) successively, at 50°C , the reactant was stirred for 72 hours, the residue was removed by filtration, and the filtrate was washed with CH 3 COOEt was extracted 4 times, the collected organic phase layer was washed 3 times with saturated potassium chloride solution, the organic phase was collected and dried with anhydrous magnesium sulfate, the solid-liquid was separated to obtain the filtrate, which was rotary evaporated at 40 °C and dried in vacuo to obtain the desired yellow needle. shape crystal;

[0025] Chiral metal-organic cages [Fe 4 L 6 ](ClO 4 ) 8 Synthesis of Solvent: 1,4-bis(2-imidazole formaldehyde)butane (98.4mg), (R)-1-phenylethylamine (97.8mg) and Fe(ClO 4 ) 2 ·6H 2 O (96.8 mg) was added to 20 mL of acetoni...

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Abstract

The invention discloses a chiral MOC liquid chromatography separation column for the resolution of racemic compounds. Chiral metal organic cage [Fe4L6](ClO4)8.Solvent particles are used as the stationary phase of high performance liquid chromatography, and chiral metal organic cage [Fe4L6](ClO4)8.Solvent crystals are formed by molecularly self-assembling 1,4-di(2- imidazolecarboxaldehyde)butane, (R)-1-phenylethylamine and Fe(ClO4)2.6H2O. The chiral column has good chiral recognition ability for seven racemic compounds. The chiral metal organic cages (MOCs) used as the stationary phase for liquid chromatography separation to resolute the racemic compounds have the advantages of cheap and easily available materials for synthesis, low column production cost, high separation speed, good stability and repeated use, open up a new way for the application of porous materials in the field of separation science, and have a good application prospect in the field of chiral recognition.

Description

technical field [0001] The invention belongs to the technical field of liquid chromatography separation, and in particular relates to a chiral MOC liquid chromatography column prepared by using a novel metal-organic cage material with good chiral recognition performance as a stationary phase. Background technique [0002] Chirality is an essential property of nature and plays an important role in many fields such as pharmacology, agrochemistry, biology, and chemistry. The most important driving force for the study of chiral recognition comes from chiral drugs. In commonly used drugs, most of them exist as racemates. A series of actions of chiral drugs in vivo are closely related to their configurations, and there are significant differences in the biological activities and toxicity of enantiomers with different optical activities. Therefore, the separation and acquisition of single enantiomers of chiral drugs has become an urgent need of society. In view of the importance...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29B01J20/30C07B57/00C07D209/08C07D487/04C07C315/06C07C317/14C07C213/10C07C217/32C07D301/32C07D303/04C07C29/74C07C33/46C07D307/48
CPCB01J20/29C07B57/00C07B2200/07C07C29/74C07C213/10C07C315/06C07D209/08C07D301/32C07D303/04C07D307/48C07D487/04C07C2603/24C07C317/14C07C217/32C07C33/46
Inventor 谢生明余云艳李丽袁宝燕
Owner YUNNAN NORMAL UNIV
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