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New pirkle-type chiral fixed phase and its prepn process

A chiral stationary phase and reaction technology, applied in the field of chiral separation, to achieve the effect of simple reaction route, easy industrialization, and easy operation

Inactive Publication Date: 2006-03-01
SHENYANG PHARMA UNIVERSITY
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Problems solved by technology

[0004] Pirkle-type chiral stationary phases are currently the most widely used and most widely used chiral stationary phases, but most of them are single π-base (bringing electron substituents) chiral stationary phases (such as Naphthylleucine) Or π-acid type (with electron-withdrawing substituent) chiral stationary phase (such as Pirkle-1J, α-Burke-2, etc.), which can only be used for π-electron acceptor compounds or π-electron donor compound enantiomers separation

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  • New pirkle-type chiral fixed phase and its prepn process
  • New pirkle-type chiral fixed phase and its prepn process

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Embodiment 1

[0018] Dissolve 1.21g (4.26mmol) of R-(+)-1,1'-binaphthyl-2,2'-diamine in 100ml of dichloromethane, add 0.59ml (4.26mmol) of triethylamine, and mix The solution was placed in a 250ml double-necked round-bottomed flask; 0.98g (4.26mmol) of 3,5-dinitrobenzoyl chloride (DNB-Cl) was dissolved in 80ml of dichloromethane, and the solution was dissolved at room temperature under nitrogen protection. Drop it into the above stirring mixed solution as slowly as possible. After dropping, the resulting mixture was heated to reflux for 10 hours. After cooling, the reaction mixture was washed with 2mol / L hydrochloric acid solution (100ml×3), the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated to dryness. The product was separated by silica gel column chromatography to obtain 1.79g of a red powdery solid. 1 Confirmed by H-NMR as N-[2'-amino-[1,1']binaphthyl-2-]-3,5-dinitrobenzamide, yield: 88%.

[0019] Dissolve 1.79g (3.74mmol) of it in 100ml of di...

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Abstract

The present invention is new Pirkle-type chiral fixed phase and its preparation process. The process adopts R-(+)-1, 1í»-binaphthyl-2, 2í»-diamine as initial material and prepares the target product through two reaction steps. The Pirkle-type chiral fixed phase has in its molecular structure both electron donor binaphthyl radical and electron acceptor 3, 5-dinitro benzoyl radical, has several sites capable of generating hydrogen bond effect with analyte and can generate certain spatial stereo chemical effect. The Pirkle-type chiral fixed phase is important one with wide application range and has excellent separation effect. The two-step reaction process has total yield up to 42.24 %, simple reaction line, easy operation and easy application in industrial production.

Description

Technical field: [0001] The invention relates to the technical field of chiral separation, in particular to a novel Pirkle-type chiral stationary phase and a preparation method. Background technique: [0002] Chirality is a basic feature of biological systems. Biomacromolecules, such as proteins, polysaccharides, carriers, receptors, nucleic acids, and enzymes, which are important foundations of life activities, all have chiral characteristics, and the pharmacological effects of chiral enantiomer drugs It is achieved through strict chiral matching and molecular recognition with macromolecules in vivo. In many cases, there are significant differences in the pharmacological activity, metabolic process, metabolic rate and toxicity of a pair of enantiomers of a compound in vivo. Therefore, the separation and determination of chiral drugs is of great significance for studying the pharmacokinetic process of chiral drugs in vivo, determining pharmacokinetic parameters, pharmacolog...

Claims

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Application Information

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IPC IPC(8): C07F9/18C07C275/40C07C233/80C09B63/00
Inventor 李发美张丹丹玄明浩
Owner SHENYANG PHARMA UNIVERSITY
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