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Chiral derivatization reagent, and preparation method and application thereof

A technology for derivatization reagents and chiral compounds, which is applied in the field of chiral derivatization reagents and their preparation, can solve the problems of ineffective analysis of aromatic amine chiral substances and slow dissociation rate, and achieves simple and easy experimental operation. The effect of high efficiency, high chemical shift discrimination, and mild reaction conditions

Active Publication Date: 2021-07-23
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Fluorine-containing chiral derivatization reagents have been reported in the determination of various amine chiral substances; for example, D.A. ) for the analysis of aliphatic amine chiral substances [2] , however, this method cannot effectively analyze chiral aromatic amines; fluorine-containing chiral palladium complexes have also been used to determine chiral amines [3] , based on the exchange of acetonitrile weakly bound to palladium by the chiral Lewis base analyte, resulting in different 19 F NMR signals are used to analyze and identify the enantiomers of chiral substances. However, this method requires the complex to be closely combined with the analyte, and the dissociation rate is very slow, so that the corresponding NMR signals can be measured.

Method used

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  • Chiral derivatization reagent, and preparation method and application thereof
  • Chiral derivatization reagent, and preparation method and application thereof
  • Chiral derivatization reagent, and preparation method and application thereof

Examples

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preparation example Construction

[0052] The present invention also provides a preparation method of a chiral derivatization reagent represented by formula (I), comprising the following steps:

[0053] The first compound is dissolved in ethanol, and the first compound is selected from any of 2-fluoro-4-nitrobenzaldehyde, 3-fluoro-5-nitrobenzaldehyde, and 4-fluoro-3-nitrobenzaldehyde A kind; The second compound is dissolved in deionized water, and the second compound is selected from the group consisting of trans-4-fluoro-L-proline, cis-4-fluoro-L-proline, trans-4- Any one of fluoro-D-proline or cis-4-fluoro-D-proline;

[0054] The molar ratio of the first compound to the second compound is less than 1.0, the two are mixed, the pH of the mixed solution is adjusted to 10-10.5, and the reaction is carried out at room temperature for 15 minutes to obtain the compound of the formula (I) A chiral derivatization reagent is shown.

[0055] In the present invention, the F substituent on the benzene ring in the first ...

Embodiment 1

[0068] Preparation of a fluorine-containing chiral derivatization reagent (c):

[0069] Dissolve 5.0 mM 2-fluoro-4-nitrobenzaldehyde (2F5NBA) in ethanol, and 7.5 mM trans-4-fluoro-L-proline in deionized water, mix the two, and mix The molar ratio of 2-fluoro-4-nitrobenzaldehyde (2F5NBA) to trans-4-fluoro-L-proline in the solution was 1:1.5, and 50 mM NaOH was added to adjust the pH of the solution to 10.5. The reaction was carried out at 25°C for 15 min, and a fluorine-containing chiral derivatization reagent (c) was obtained. The chemical equation is as attached figure 1 As shown, the mass spectrum of the product is shown in the attached image 3 As shown, the obtained mass spectrum data are as follows:

[0070] ESI-MS: 283.07211, theoretical value: [M+H] + : 283.06520.

[0071] The yield of the product can be calculated from the ratio of the integral area of ​​the fluorine spectrum of the raw material and the chiral derivatization reagent to be 94%.

Embodiment 2

[0073] Preparation of a fluorine-containing chiral derivatization reagent (c1):

[0074] The rest is the same as in Example 1, except that the raw material "2-fluoro-4-nitrobenzaldehyde (2F5NBA)" is changed to "3-fluoro-5-nitrobenzaldehyde (3F5NBA)", "add 50 mMNaOH adjusts the pH of the solution to be 10.5" to "adding 50 mMNaOH to adjust the pH of the solution to be 10" to obtain a fluorine-containing chiral derivatization reagent (c1) with a yield of 95%, and the chemical equation is as attached Figure 4 shown.

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Abstract

The invention discloses a fluorine-containing chiral derivatization reagent, and a preparation method and application thereof. The fluorine-containing chiral derivatization reagent shown in the formula (I) is synthesized through substitution reaction of fluoro-nitrobenzaldehyde and fluoro-proline, raw materials are cheap and easy to obtain, reaction conditions are mild, and experimental operation is easy and convenient to implement; the fluorine-containing chiral derivatization reagent is applied to detection and analysis of primary amine chiral substances, the chiral derivatization reagent and the primary amine chiral substances are covalently connected and are firmly combined, <19>F NMR chemical signal peaks generated by derivatized products are strong, and compared with F spectrum peaks of raw materials, the <19>F NMR chemical signal peakshave characteristics of high chemical shift discrimination. Chiral compound identification is achieved without product separation and purification, the detection method is rapid and simple, and detection by using the fluorine-containing chiral derivatization reagent can achieve the identification and analysis of aliphatic primary amine chiral substances, and can effectively identify aromatic primary amine chiral substances.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a chiral derivatization reagent and its preparation method and application. Background technique [0002] Chirality is a fundamental property of nature and plays a vital role in life processes and material creation; the rapid detection and identification of chiral compounds is of great significance in synthetic chemistry, medicinal chemistry, and biochemistry. Since the importance of chirality was recognized, the demand for pure optical compounds in various fields has greatly increased, which has promoted the development of chiral detection and analysis techniques, such as chromatography, CD spectroscopy, fluorescence, nuclear magnetic resonance NMR, etc. [1] . Compared with other methods, NMR provides a facile method for a large number of compounds, and can obtain rich qualitative and quantitative structural information in a multidimensional manner at the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/16G01N24/08
CPCC07D207/16G01N24/088C07B2200/07
Inventor 黄碧玲黄少华赵玉芬
Owner NINGBO UNIV