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Preparation method of nitrophenylcarbamate full-derived beta-cyclodextrin bonded ordered mesoporous SBA-15 chiral stationary phase

A nitrophenylcarbamate, chiral stationary phase technology, applied in chemical instruments and methods, other chemical processes and other directions, can solve the problems of high mobile phase cost and stationary phase loss, and achieves low preparation cost and stable performance. , the effect of high bonding

Inactive Publication Date: 2014-06-25
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cellulose is the most widely used, but this type of stationary phase is mainly coating type, the loss of stationary phase makes the choice of mobile phase limited and the cost is high

Method used

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  • Preparation method of nitrophenylcarbamate full-derived beta-cyclodextrin bonded ordered mesoporous SBA-15 chiral stationary phase
  • Preparation method of nitrophenylcarbamate full-derived beta-cyclodextrin bonded ordered mesoporous SBA-15 chiral stationary phase
  • Preparation method of nitrophenylcarbamate full-derived beta-cyclodextrin bonded ordered mesoporous SBA-15 chiral stationary phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Take SBA-15 (400 m 2 / g) Activated silica gel 2.5 g as the base.

[0025] (1) Under a nitrogen atmosphere, according to the ratio of β-cyclodextrin (mmol): anhydrous pyridine (mL): p-toluenesulfonyl chloride (mmol): anhydrous pyridine (mL) of 1 : 10 : 0.9 : 2.5, Dissolve β-cyclodextrin in anhydrous pyridine, dissolve p-toluenesulfonyl chloride in anhydrous pyridine and add dropwise to the above solution, stir for 2 h, and stir at room temperature for 10 h. After the solution turns yellow, remove pyridine in vacuum, add Anhydrous diethyl ether gave a white solid, which was filtered and recrystallized several times with ultrapure water to obtain the 6-oxo-tosylated-β-cyclodextrin intermediate ( ). Under nitrogen atmosphere, according to the intermediate ( ) (mmol): sodium azide (mmol): anhydrous N, N-dimethylformamide (mL) is a ratio of 1: 0.9: 12, the intermediate ( ) was dissolved in anhydrous N,N-dimethylformamide, added sodium azide, and stirred at room tempera...

Embodiment 2

[0033] Take SBA-15 (500 m 2 / g) Activated silica gel 2.5 g as the base.

[0034] (1) Under nitrogen atmosphere, according to the ratio of β-cyclodextrin (mmol): anhydrous pyridine (mL): p-toluenesulfonyl chloride (mmol): anhydrous pyridine (mL) of 1 : 12 : 1.1 : 3.0, Dissolve β-cyclodextrin in anhydrous pyridine, dissolve p-toluenesulfonyl chloride in anhydrous pyridine, add dropwise to the above solution and stir for 3 h, and stir at room temperature for 12 h. After the solution turns yellow, remove pyridine in vacuum, add Anhydrous diethyl ether gave a white solid, which was filtered and recrystallized several times with ultrapure water to obtain the 6-oxo-tosylated-β-cyclodextrin intermediate ( ). Under nitrogen atmosphere, according to the intermediate ( ) (mmol): sodium azide (mmol): anhydrous N, N-dimethylformamide (mL) is a ratio of 1: 1.1: 14, the intermediate ( ) was dissolved in anhydrous N,N-dimethylformamide, added sodium azide, and stirred at room temperatu...

Embodiment 3

[0041] Embodiment 3 split experiment

[0042] The fully derivatized β-cyclodextrin-bonded SBA-15 silica gel chiral stationary phase containing nitrophenylcarbamate in Example 3 was used for the separation of chiral drugs.

[0043] Split object: three β-receptor blockers atenolol, metoprolol, esmolol structure see figure 2 .

[0044]Specific process: The chromatographic column is filled by the homogenate filling method. Using acetone as the homogenizer and methanol as the displacing agent, the homogenate was packed into a cleaned chromatographic column (150 mm × 4.6 mm I.D.) under a pressure of 5000 psi, and the pressure was maintained for 30 min. Remove the packed chromatographic column, put on the chromatographic column head, and mark the direction of mobile phase. Rinse the chromatographic column repeatedly with water and methanol, equilibrate with the mobile phase used, and inject the sample after the baseline is stable. The standard substance was made into a stock sol...

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Abstract

The invention relates to a preparation method of a bonded SBA-15 silica gel chiral stationary phase. The preparation method comprises the major steps of firstly, preparing an azido-containing beta-cyclodextrin ligand from beta-cyclodextrin in an anhydrous solvent, secondly, preparing alkynyl-containing bonded ordered mesoporous SBA-15 silica gel from 3-aminopropyltriethoxysiloxane and propynoic acid, thirdly, bonding the azido-containing beta-cyclodextrin to the surface of the SBA-15 silica gel by virtue of a click reaction by taking anhydrous N,N-dimethylformamide as a solvent and CuI(PPh3) as a catalyst, and fourthly, modifying the product of the third step by using a nitro-containing phenyl isocyanate with anhydrous N,N-dimethylformamide as a solvent, and reacting to obtain the nitrophenylcarbamate full-derived beta-cyclodextrin bonded SBA-15 silica gel chiral stationary phase. The preparation method is simple and convenient, low in cost and wide in applicability.

Description

technical field [0001] The invention relates to a preparation method of a bonded SBA-15 silica gel chiral stationary phase, in particular to a bonded SBA-15 silica gel chiral stationary phase with nitrophenyl carbamate-containing fully derivatized β-cyclodextrin as a ligand Preparation method of stationary phase. Background technique [0002] Chirality is a basic property of nature, which refers to the property that a substance and its mirror image cannot overlap. Many molecules related to life, such as DNA, enzymes, antibodies, etc., have chirality, and their interactions with the R-, S-enantiomers of chiral drugs show high stereoselectivity, making the drug enantiomers There are certain differences in their efficacy, pharmacology and toxicology. For example, the thalidomide incident that occurred in Europe in the 1960s was a bitter lesson. The analgesic thalidomide, which is used to reduce pregnancy reactions in pregnant women, has its efficacy from the R-enantiomer, whi...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08B37/16C08G77/388B01J20/29B01J20/30
Inventor 李来生周仁丹黄志兵程彪平聂桂珍张宏福
Owner NANCHANG UNIV
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