Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for measuring optical purity of chiral carboxylic acid

A measurement method and optical purity technology, which is applied in the field of rapid determination of the optical purity of chiral carboxylic acids, can solve problems such as difficult synthesis, narrow application range, and inability to achieve baseline separation, and achieve good repeatability and wide application range.

Inactive Publication Date: 2013-09-11
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
View PDF11 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method only needs to dissolve a very small amount of chiral chemical shift reagent and carboxylic acid substrate in a deuterated solvent and then simply mix it in an NMR tube to test. Except for ordinary NMR instruments, no other special equipment is required, and the analysis speed is fast. Fast, easy to operate, low test cost and other outstanding advantages, so in recent decades there have been related research reports, and various types of chiral shift reagents (CSR) have been developed for the analysis of chiral carboxylic acids, such as Amines, aminoalcohols, diamines, amides, macrocycles, ureas (thioureas), but most of them are due to the chiral character of the enantiomers of carboxylic acids 1 The H chemical shift difference is too small to achieve baseline separation, and a small number of chemical shift differences are large and relatively effective, but there are problems such as synthesis difficulties or narrow application ranges, so the synthesis is simple, convenient, practical, and efficient chiral chemical shift reagents further research is needed

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for measuring optical purity of chiral carboxylic acid
  • Method for measuring optical purity of chiral carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0023] Example 1 Determination of Optical Purity of Mandelic Acid Mixed Configuration Sample

[0024] Take racemic mandelic acid, optically pure R-mandelic acid, mandelic acid sample to be tested, N,N-dimethyl-4-aminopyridine, chiral shift reagent (S,S)-1,2-di[( 3,5-bistrifluoromethylphenyl)thioureido]-1,2-diphenylethane were prepared into 15 mMol / L deuterated chloroform solution for later use. First, take 0.2 mL of the prepared racemic mandelic acid deuterated chloroform solution and add 0.4 mL of deuterated chloroform, mix well, put it into a 400 MHz nuclear magnetic resonance instrument and record at room temperature 1 H NMR signal, in (δ H = 0) as the internal standard to obtain the chemical shift of mandelic acid α-H as δ= 5.26; each take 0.2 mL of prepared racemic mandelic acid and N, N-dimethyl-4-aminopyridine, chiral shift reagent After adding the same NMR tube and mixing, put it into a 400 MHz NMR instrument and record at room temperature 1 H NMR signal, in (δ H ...

example 2

[0026] Example 2 Determination of Optical Purity of 2-Phenylpropionic Acid Mixed Configuration Sample

[0027] Take racemic 2-phenylpropionic acid, optically pure R-2-phenylpropionic acid, 2-phenylpropionic acid sample to be tested, N,N-dimethyl-4-aminopyridine, chiral shift reagent ( S, S)-1,2-bis[(3,5-bistrifluoromethylphenyl)thioureido]-1,2-diphenylethane were prepared in 15 mMol / L deuterated chloroform solution spare. First, take 0.2 mL of the prepared racemic 2-phenylpropionic acid deuterated chloroform solution and add 0.4 mL of deuterated chloroform, mix well, put it into a 400 MHz nuclear magnetic resonance instrument and record at room temperature 1 H NMR signal, in (δ H = 0) as internal standard to obtain 2-phenylpropanoic acid CH 3 The chemical shift of -H is δ= 1.53; take 0.2 mL of prepared racemic 2-phenylpropionic acid and N, N-dimethyl-4-aminopyridine, and chiral shift reagent into the same NMR tube, mix and release recorded in a 400 MHz NMR instrument at r...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a method for measuring the optical purity of chiral carboxylic acid by use of a chiral chemical shift reagent. A series of chiral diamines such as 1,2-diphenylethylenediamine, cyclohexyldiamine and dithio (diurea) derivatives of binaphthyldiamine are used as chiral shift reagents, and the optical purity of the chiral carboxylic acid is quickly detected by a nuclear magnetic resonance spectrometer. The method provided by the invention has the advantages of easy synthesis of shift reagents and simplicity in operation, and is a quick, efficient, convenient and practical detection means.

Description

technical field [0001] The present invention is in the field of determining the optical purity of chiral compounds. The invention is a new method for quickly measuring the optical purity of chiral carboxylic acid. Background technique [0002] Chiral carboxylic acids are important structural units in natural products and drug molecules, and are also important intermediates in organic synthesis. Therefore, it is particularly important to develop a fast, convenient and accurate method for determining the optical purity of chiral carboxylic acids. In the past few decades, many methods to detect the optical purity of chiral carboxylic acids have been developed, such as high performance liquid chromatography, gas chromatography, capillary electrophoresis, and nuclear magnetic resonance, etc. Among these methods, nuclear magnetic resonance resolution using chiral shift reagents is currently one of the most rapid and environmentally friendly methods for determining the optical pur...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): G01N24/08
Inventor 宋玲边广岭杨士伟
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com