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

Synthetic method of maleimide phosphatidyl ethanolamine

A technology of hydroxysuccinimide and compounds, applied in the field of preparation of maleimidated phosphatidylethanolamine, which can solve the problems of difficult separation and purification of by-products, time-consuming and labor-intensive problems

Inactive Publication Date: 2010-07-07
SHANGHAI INST OF PHARMA IND
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method uses N,N-dicyclohexylcarbodiimide to produce by-product separation and purification difficulties, the final yield is only about 30%, and the cross-linking agent reacts with phosphatidylethanolamine to generate maleimidated phosphatidylethanolamine The process is extremely time-consuming and laborious

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
  • Synthetic method of maleimide phosphatidyl ethanolamine
  • Synthetic method of maleimide phosphatidyl ethanolamine
  • Synthetic method of maleimide phosphatidyl ethanolamine

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0047] 1. The preparation method provided by the invention has a high yield of the compound of formula I;

[0048] 2. The preparation method provided by the invention saves time;

[0049] 3. The preparation method provided by the invention reduces the cost.

Embodiment 1

[0054] Preparation of Formula I Compound A

[0055] The first step: Add 300ml tetrahydrofuran, m-aminobenzoic acid (20g, 0.146mol) and maleic anhydride (15.7g, 0.166mol) into a 500ml three-necked flask, react at room temperature for 1 hour, and filter with a Buchner funnel to obtain a light yellow solid , and dried to obtain 28.76g of the compound of formula II, with a yield of 87.40%, m.p.: 206-208°C.

[0056] The second step: add 150ml of acetic anhydride, the compound of formula II (15g, 0.0638mol) and anhydrous sodium acetate (7.5g, 0.091mol) obtained in the first step to a 250ml three-necked bottle, and stir at a high speed in an oil bath at 90°C for 3h , the solution turned dark yellow, the reaction solution was poured into ice water containing 300ml of water, stirred for 3h, a yellow precipitate was produced, the crude product of the compound of formula III was obtained by filtration, and 11.35g of the compound of formula III was obtained by recrystallization with absol...

Embodiment 2

[0064] Preparation of Formula I Compound B

[0065] The first step: add 300ml tetrahydrofuran, m-aminobenzoic acid (20g, 0.146mol) and maleic anhydride (21.4g, 0.218mol) into a 500ml three-necked flask, react at room temperature for 1h, and filter with a Buchner funnel to obtain a light yellow solid , and dried to obtain 31.22g of the compound of formula II, with a yield of 91.40%, m.p.: 206-208°C.

[0066] The second step: add 100ml of acetic anhydride, the compound of formula II obtained in the first step (15g, 0.0638mol) and anhydrous sodium acetate (5.21g, 0.064mol) in a 250ml three-necked bottle, and stir at a high speed in an oil bath at 90°C for 3h. The solution turned dark yellow, and the reaction solution was poured into ice water containing 300ml of water, stirred for 3 hours, a yellow precipitate was produced, filtered to obtain the crude compound of formula III, and recrystallized with absolute ethanol to obtain 10.38 g of compound of formula III, with a yield of 7...

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 discloses a preparation method of a compound as shown in the formula I. The method comprises the following steps: (1) M-aminobenzoic acid and maleic anhydride are mixed and reacted to obtain the compound as shown in the formula II. (2)The compound of formula II and acetic anhydride are mixed and reacted to obtain the compound as shown in the formula III.(3) The compound of the formula III, N-hydroxysuccinimide and 1-ethyl-3-(3-dimethylaminopropyl)-carbonyl diimine hydrochloride are mixed and reacted to obtain the compound as shown in the formula IV. And (4) the compound of the formula IV and phosphatidyl ethanolamine are reacted in mixed solvents to obtain the compound as shown in the formula I. The mixed solvent consists of chloroform, methanol and water, the volume ratio thereof is 9: 1: 0.1-9: 0.5; wherein, R represents aliphatic hydrocarbon of C11\C13\C15\C17.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of maleimidated phosphatidylethanolamine. Background technique [0002] Liposomes were discovered by British scholar Bangham in the 1960s by dispersing phospholipids in water. In the 1970s, liposomes were used as drug carriers by Rymen et al. In the mid-1980s, some companies engaged in liposome development were established one after another, and new liposomes such as antineoplastic drugs and vaccines were developed. With the development of polymer chemistry and molecular biology combined with liposome research, functional liposomes with long circulation and targeting have been developed. [0003] Phospholipids are the main components of liposome bilayer membranes, including natural phospholipids and synthetic phospholipids. Maleimidated phosphatidylethanolamine is a synthetic phospholipid. This functional phospholipid is often used in the preparation of t...

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): C07F9/572
Inventor 邓家欣蔡正艳陶涛
Owner SHANGHAI INST OF PHARMA IND
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