Preparation method of novel phenylalanine chiral chromatographic column stationary phase

A technology of chiral chromatographic column and phenylalanine, which is applied in the field of preparation of new chiral chromatographic column stationary phase, which can solve the problems of easy loss of stationary phase, tailing of effluent components, and limited service life, etc.

Active Publication Date: 2015-01-21
上海可力梅塔生物医药科技有限公司 +3
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage is that the separation takes a long time, the tailing of the last effluent components is serious, and the stationary phase is easy to lose, which limits its service life
A Chinese patent application (application number CN200480043803.X) discloses a chemically bonded chiral stati

Method used

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  • Preparation method of novel phenylalanine chiral chromatographic column stationary phase
  • Preparation method of novel phenylalanine chiral chromatographic column stationary phase
  • Preparation method of novel phenylalanine chiral chromatographic column stationary phase

Examples

Experimental program
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specific Embodiment 1

[0040] Specific Example 1: Preparation of L-phenylalanine chiral stationary phase CSP1

[0041] 1. Pretreatment of the carrier:

[0042] Take 5.0g of silica gel balls, put them into an eggplant-shaped bottle, add 10mL of 12mol / L concentrated hydrochloric acid, heat to reflux for 2h, filter, wash with water until neutral, rinse with acetone and anhydrous ether in turn, and dry in vacuum. .

[0043] 2. Synthesis of Chiral Monomers

[0044] 1) Synthesis of Z-L-PheCOOH

[0045]Add 0.5 mol of NaOH to a three-neck flask containing 1.0 L of deionized water under ice-water bath, stir to dissolve, then add 0.5 mol of L-PheCOOH, stir to completely dissolve, add dropwise 0.5 mol of benzyloxychloride and 0.5 mol NaOH with the same volume of deionized aqueous solution, stirred at room temperature for 12 hours. Extract with ether, add concentrated hydrochloric acid to the extracted water phase, adjust the pH value to 2-3, add ethyl acetate for extraction, wash with water until neutral, ...

specific Embodiment 2

[0058] Specific Example 2: Preparation of L-phenylalanine chiral stationary phase CSP2

[0059] 1. Pretreatment of the carrier:

[0060] Take 5.0g of silica gel balls, put them into an eggplant-shaped bottle, add 10mL of 12mol / L concentrated hydrochloric acid, heat to reflux for 2h, filter, wash with water until neutral, rinse with acetone and anhydrous ether in turn, and dry in vacuum.

[0061] 2. Synthesis of Chiral Monomers

[0062] 1) Synthesis of Z-L-PheCOOH

[0063] Add 0.5 mol of NaOH to a three-neck flask containing 1.0 L of deionized water under ice-water bath, stir to dissolve, then add 0.5 mol of L-PheCOOH, stir to completely dissolve, add dropwise 0.5 mol of benzyloxychloride and 0.5 mol NaOH with the same volume of deionized aqueous solution, stirred at room temperature for 12 hours. Extract with ether, add concentrated hydrochloric acid to the extracted water phase, adjust the pH value to 2-3, add ethyl acetate for extraction, wash with water until neutral, an...

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Abstract

The invention provides a preparation method of a novel chiral chromatographic column stationary phase based on phenylalanine. The preparation method comprises the following steps: 1, carrying out surface treatment on a silica gel sphere; 2, preparing a phenylalanine chiral selector monomer; and 3, preparing the chiral chromatographic column stationary phase. The method has the advantages of simple process route, low cost and operation convenience, and the prepared chiral chromatographic column stationary phase has the advantages of wide chiral selectivity, wide mobile phase application range, good bonding force, difficult loss, long service life, short separation time, no tailing, high column efficiency and the like.

Description

technical field [0001] The invention relates to the field of liquid chromatography chiral separation, in particular to a preparation method of a novel chiral chromatography column stationary phase based on phenylalanine. Background technique [0002] Chirality is one of the essential properties of nature on which human beings depend. The chemical processes in life phenomena are carried out in a highly asymmetric environment. It is well known that a single optically pure enantiomer in a chiral compound exhibits different properties such as toxicity, pharmacology, and biological activity. Therefore, the separation and purification of enantiomers has received more and more attention in many scientific fields such as pharmaceuticals. [0003] More than 60% of the drug molecules currently on the market contain one or more chiral centers, and most of these chiral drugs are sold in the market in the form of racemic. However, chiral drugs often have only one of the enantiomers as ...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30B01D15/38
CPCB01D15/3833B01J20/29
Inventor 杨永刚李艺李宝宗王庆峰
Owner 上海可力梅塔生物医药科技有限公司
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