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Synthetic method of maleimide phosphatidyl ethanolamine

A technology of hydroxysuccinimide and compound is applied in the field of preparation of maleimidized phosphatidylethanolamine, and can solve the problems of difficulty in separation and purification of by-products, time-consuming and laborious problems, etc.

Inactive Publication Date: 2012-12-05
SHANGHAI INST OF PHARMA IND CO LTD
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  • 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

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

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preparation example Construction

[0054] 1. The preparation method provided by the invention has a high yield of the compound of formula I;

[0055] 2. The preparation method provided by the invention saves time;

[0056] 3. The preparation method provided by the invention reduces the cost.

Embodiment 1

[0061] Preparation of Formula I Compound A

[0062] 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.

[0063] The second step: add 150ml of acetic anhydride, the formula II compound (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 absolute...

Embodiment 2

[0071] Preparation of Formula I Compound B

[0072] 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.

[0073] 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...

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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

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/572
Inventor 邓家欣蔡正艳陶涛
Owner SHANGHAI INST OF PHARMA IND CO LTD
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