Preparation method of vinyl sulfone derivatives

A technology for vinyl sulfone and derivatives, which is applied in the field of preparation of polyethylene glycol vinyl sulfone derivatives, can solve the problems of low yield and difficult separation of polyethylene glycol, and achieve high conversion rate, fast reaction speed, The effect of good application value

Active Publication Date: 2016-08-03
DALIAN UNIV OF TECH
View PDF5 Cites 17 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The patent (US5414135) introduces a method for preparing polyethylene glycol vinyl sulfone derivatives using sodium hydroxide solution. Due to the competitive reaction of water molecules in the reaction system, t

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
  • Preparation method of vinyl sulfone derivatives
  • Preparation method of vinyl sulfone derivatives
  • Preparation method of vinyl sulfone derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] DMAP catalyzed the preparation of methyl tripolyethylene glycol vinyl sulfone derivatives (n=3):

[0031] Take 1mL of methyl tripolyethylene glycol (Me-PEG 3 ) was dissolved in 4 mL of divinyl sulfone (DVS), 60 mg of DMAP was added, reacted for 2 hours at room temperature, and purified by column chromatography to obtain methyl tripolyethylene glycol vinyl sulfone derivatives (93% yield). 1 HNMR (400MHz,D 2 O): δ6.63(dd,1H,SO 2 CH=CH 2 ),6.42(d,1H,SO 2 CH=CH 2 ),6.18(d,1H,SO 2 CH=CH 2 ), 3.91(t,2H,SO 2 CH 2 CH 2 ),3.57(t,2H,SO 2 CH 2 CH 2 OCH 2 ),3.48(t,2H,SO 2 CH 2 CH 2 ),3.33(m,3H,CH 3 O),3.63(m,10H,othersCH 2 ).

Embodiment 2

[0033] Triphenylphosphine catalyzed the preparation of methyl tripolyethylene glycol vinyl sulfone derivatives (n=3):

[0034] Take 1mL of methyl tripolyethylene glycol (Me-PEG 3 ) was dissolved in 4mL divinyl sulfone (DVS), and 125 mg triphenylphosphine was added, reacted for 2 hours at room temperature, purified by column chromatography to obtain methyl tripolyethylene glycol vinyl sulfone derivative (yield was 76%) . 1 HNMR (400MHz,D 2 O): δ6.63(dd,1H,SO 2 CH=CH 2 ),6.42(d,1H,SO 2 CH=CH 2 ),6.18(d,1H,SO 2 CH=CH 2 ), 3.91(t,2H,SO 2 CH 2 CH 2 ),3.57(t,2H,SO 2 CH 2 CH 2 OCH 2 ),3.48(t,2H,SO 2 CH 2 CH 2 ),3.33(m,3H,CH 3O),3.63(m,10H,othersCH 2 ).

Embodiment 3

[0036] 1-Methylimidazole catalyzes the preparation of methyl tripolyethylene glycol vinyl sulfone derivatives (n=3):

[0037] Take 1mL of methyl tripolyethylene glycol (Me-PEG 3 ) was dissolved in 4mL divinylsulfone (DVS), added 40mg1-methylimidazole, reacted for 2 hours at room temperature, and purified by column chromatography to obtain methyl tripolyethylene glycol vinylsulfone derivatives (yield: 32%) . 1 HNMR (400MHz,D 2 O): δ6.63(dd,1H,SO 2 CH=CH 2 ),6.42(d,1H,SO 2 CH=CH 2 ),6.18(d,1H,SO 2 CH=CH 2 ), 3.91(t,2H,SO 2 CH 2 CH 2 ),3.57(t,2H,SO 2 CH 2 CH 2 OCH 2 ),3.48(t,2H,SO 2 CH 2 CH 2 ),3.33(m,3H,CH 3 O),3.63(m,10H,othersCH 2 ).

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 relates to a preparation method of vinyl sulfone derivatives. The vinyl sulfone derivatives have the structure disclosed as General Formula I. According to the preparation method, compounds i react with divinyl sulfone in the presence of a catalyst, wherein R is selected from H or C1-C8 alkyl; n is a whole number which is greater than or equal to 1; and the catalyst is selected from triaryl phosphine compounds or nitrogen heterocycle compounds. Under the action of the selected catalyst, the reaction can quickly occur under room temperature conditions to obtain the products. The method has the advantages of mild conditions, high reaction speed, high conversion rate and the like. The prepared products have the advantages of hydrolysis resistance, alkali resistance, broad reaction spectrum and the like, and have very high application value.

Description

technical field [0001] The invention relates to a preparation method of a class of vinyl sulfone derivatives, especially polyethylene glycol vinyl sulfone derivatives. technical background [0002] Polyethylene glycol is a kind of macromolecular polymer with unique physical and chemical properties. It has good water solubility and can also be dissolved in various organic solvents. The PEGylation of biomolecules can improve their properties in many aspects, such as increasing the solubility in water and organic solvents, significantly increasing the acid-base stability and thermal stability of biomolecules, and enhancing their stability to enzymes Wait. Especially for drug molecules, PEGylation can improve the solubility and circulation time of drugs in the body, thereby improving the bioavailability of drugs and reducing the number of medications. [0003] In view of the important role of PEGylation in biomedicine, a variety of polyethylene glycol derivatives have been dev...

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): C07C315/04C07C317/18C08G65/48
CPCC07C315/04C08G65/48C07C317/18
Inventor 程昉王汉奇孙澹逸何炜曲景平
Owner DALIAN UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap