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

Method for resolution of 2,3-dimercapto propanol raceme

A dimercaptopropanol, racemate technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effect of precise medication

Inactive Publication Date: 2013-11-13
NEW FOUNDER HLDG DEV LLC +2
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, in the prior art, no effective method has been found to successfully resolve [R, (-)]-2,3-dimercaptopropanol and [S, (+)]-2,3-dimercaptopropanol

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 resolution of 2,3-dimercapto propanol raceme

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] 1) Under nitrogen protection, add 10g (80mmol) of dimercaptopropanol racemate to 40ml (S)-(+)-2-butanol, and add 7g (80mmol) (R)-(- )-3-methyl-2-butylamine, after the dropwise addition, continue to stir the reaction for 3h; 40mmol) of (S)-(+)-2-butanol solution, after the dropwise addition, continue to stir and react for 0.5h, let stand, and filter;

[0070] 2) Add the filter cake obtained in step 1) into 15ml of toluene, under stirring, add 40ml of toluene solution containing 80mmol hydrogen chloride, filter, concentrate, recover toluene, and obtain (R)-(-)-2,3-dimercapto Propanol 4.3g, [α]=-3.77°, the purity of 2,3-dimercaptopropanol is 98.95%;

[0071] 3) Concentrate the filtrate obtained in step 1) to recover (S)-(+)-2-butanol, add 15ml of toluene, under stirring, add 50ml of toluene solution containing 100mmol hydrogen chloride, filter, concentrate, and recover toluene to obtain (S )-(+)-2,3-dimercaptopropanol 5.0g, [α]=+3.15°, the purity of 2,3-dimercaptopropano...

Embodiment 2

[0073] 1) Under nitrogen protection, add 10g (80mmol) of dimercaptopropanol racemate to 50ml (S)-(+)-2-butanol, and drop 7g (80mmol) of (R)-(- )-3-methyl-2-butylamine, after the dropwise addition, continue to stir the reaction for 3h; 40mmol) of (S)-(+)-2-butanol solution, after the dropwise addition, continue to stir and react for 0.5h, let stand, and filter.

[0074] 2) Concentrate the filtrate obtained in step 1), add 15ml of toluene to the obtained product, add 50ml of toluene dilution solution containing 100mmol hydrogen chloride under stirring, filter, concentrate, and recover toluene to obtain (S)-(+)-2, 5.1 g of 3-dimercaptopropanol, [α]=+2.85°, the purity of 2,3-dimercaptopropanol is 98.71%.

[0075] 3) Add the filter cake obtained in step 1) into 15ml of toluene, under stirring, add 80ml of toluene solution containing 80mmol hydrogen chloride, filter, concentrate, and recover toluene to obtain (R)-(-)-2,3-dimercapto 3.9 g of propanol, [α]=-3.92°, and the purity of ...

Embodiment 3

[0077]1) Under nitrogen protection, add 10g (80mmol) of dimercaptopropanol racemate to 30ml (S)-(+)-2-butanol, and drop 7g (80mmol) of (R)-(- )-3-methyl-2-butylamine, after the dropwise addition, continue to stir the reaction for 3h; 80mmol) of (S)-(+)-2-butanol solution, after the dropwise addition, continue to stir and react for 0.5h, let stand, and filter.

[0078] 2) Add the filter cake obtained in step 1) into 15ml of toluene, under stirring, add 40ml of toluene solution containing 80mmol hydrogen chloride, filter, concentrate, recover toluene, and obtain (R)-(-)-2,3-dimercapto Propanol 4.5g, [α]=-3.65°, the purity of 2,3-dimercaptopropanol is 99.03%;

[0079] 3) Concentrate the filtrate obtained in step 1) to recover (S)-(+)-2-butanol, add 15ml of toluene, under stirring, add 50ml of toluene solution containing 100mmol hydrogen chloride, filter, concentrate, and recover toluene to obtain (S )-(+)-2,3-dimercaptopropanol 4.9g, [α]=+3.37°, the purity of 2,3-dimercaptoprop...

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 resolution of 2,3-dimercapto propanol raceme. The method includes 1) reacting the 2,3-dimercapto propanol raceme with a first chiral resolving agent in a chiral solvent; 2) adding a second chiral resolving agent into a mixed solution obtained by the step 1) to make the 2,3-dimercapto propanol raceme form two chiral salts with different solubility; and 3) separating the two chiral salts with different solubility through a crystallization method, and respectively carrying out acidification treatment to obtain 2,3-dimercapto propanol optically-active isomers which are separated from each other. The optical activity of the first chiral resolving agent is opposite to that of the chiral solvent, the optical activity of the second chiral resolving agent is same with that of the chiral solvent, and the first chiral resolving agent is 3-methyl-2-butylamine and the second chiral resolving agent is an alkali metal salt of a fatty alcohol. Through chiral resolution of a drug, drug use of people can be more accurate and healthy.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for resolving racemates of 2,3-dimercaptopropanol. Background technique [0002] 2,3-Dimercaptopropanol was first developed by biochemists at the University of Oxford in England during World War II as an antidote for the Lewis agent of bioweapons. It was later used in medicine as an antidote for heavy metal poisoning. Its detoxification principle is: because the sulfhydryl group (-SH) in its molecule is easy to complex with certain metals or metalloids, thus preventing its dissociation from exerting toxicity. 2,3-Dimercaptopropanol is suitable for the detoxification of arsenic, mercury, lead and other heavy metals and metalloids. In addition, 2,3-dimercaptopropanol has also been used as a drug for the treatment of Wilson's disease. [0003] The preparation method of 2,3-dimercaptopropanol can be obtained by addition and sulfhydration of allyl alcohol, th...

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
IPC IPC(8): C07C323/12C07C319/28
Inventor 彭平郭萍张洪兰王先文
Owner NEW FOUNDER HLDG DEV LLC
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