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

DMAP removal method for synthesis of cholesterol-grafted amphiphilic high-molecular material

An amphiphilic polymer and cholesterol technology, applied in the field of polymer materials, can solve the problems of difficult removal and low purification efficiency of DMAP, and achieve the effects of controllable results, favorable for industrial production and high purification efficiency.

Active Publication Date: 2018-01-23
SHENYANG PHARMA UNIVERSITY +1
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(Song Y, Tian Q, Huang Z, et al. Self-assembled micelles of novel amphiphilic copolymer cholesterol-coupled F68 containing cabazitaxel as a drug delivery system. International journal of nanomedicine, 2014, 9: 2307-2317.) The above reactions will produce a large amount of Difficult to remove DMAP-cholesterol intermediate
[0006] Therefore, in view of the low purification efficiency of DMAP in amphiphilic polymer materials grafted with cholesterol, it is urgent to develop a new method for removing DMAP efficiently and simply.

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
  • DMAP removal method for synthesis of cholesterol-grafted amphiphilic high-molecular material
  • DMAP removal method for synthesis of cholesterol-grafted amphiphilic high-molecular material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the establishment of DMAP standard curve

[0019] Weigh 10.0mg of DMAP into a 10mL volumetric flask, dilute to the mark with absolute ethanol, and shake well to obtain 1.0mg·mL of DMAP stock solution -1 . Take 0.5mL of the above DMAP stock solution into a 50mL volumetric flask, dilute to the mark with absolute ethanol, shake well, and obtain a concentration of 10.0μg·mL -1 DMAP solution. Pipette 10.0 μg·mL of the above DMAP -1 Solution 0.5, 1.0, 3.0, 5.0, 7.0, 9.0mL in a 10mL volumetric flask, dilute to the mark with absolute ethanol, shake well, the concentration is 0.5, 1.0, 3.0, 5.0, 7.0, 9.0μg·mL -1 DMAP solution, with absolute ethanol as a reference, the absorbance value was measured at 281nm with a UV-Vis spectrophotometer, and a standard curve was drawn.

[0020] Carry out linear regression on the absorbance (A) with the concentration (C), and get the regression equation A=0.1645C+0.0059 (R=0.9999), indicating that DMAP is 0.5~9.0μg·mL -1 The l...

Embodiment 2

[0021] Example 2: Solubility of different materials and DMAP intermediates in different solvents

[0022]Weigh 5.0 mg of poloxamer 188-cholesterol carbonate, polyethylene glycol 10,000 monomethyl ether cholesterol hemisuccinate, polyethylene glycol 10,000 monomethyl ether cholesterol hemisuccinate, and DMAP in vials, respectively. Add acetonitrile, diethyl ether, cyclohexane, ethyl acetate, acetonitrile and toluene to observe the solubility of different materials and DMAP in various solvents, where " / " means soluble and "↓" means insoluble. The results are shown in Table 1.

[0023] Table 1 Solubility of different materials and DMAP intermediates in solvents

[0024]

[0025] As can be seen from the above table, poloxamer 188-cholesterol carbonate, polyethylene glycol 10000 monomethyl ether cholesterol hemisuccinate, polyethylene glycol 10000 monomethyl ether cholesterol hemisuccinate and DMAP intermediates in ethanol and acetonitrile It is in the dissolved state in ether,...

Embodiment 3

[0026] Example 3: Synthesis of Poloxamer 188-cholesterol carbonate (P188-CHMC) and removal of DMAP

[0027] Take 0.04mmol poloxamer 188 (P188) in a closed container, add 0.02mmol DMAP and 0.14mmol triethylamine (TEA) under nitrogen, slowly add 0.24mmol CHM in dichloromethane (DCM) solution 16mL, Stir and mix in an ice-water bath for 30 minutes, then reflux at 45°C for 36 hours. After the reaction was completed, the solvent was removed under reduced pressure, and a white wax was obtained by precipitation with glacial ether, and the precipitate was washed repeatedly with ether three times (to remove unreacted CHM) to obtain the crude product of P188-CHMC in powder form.

[0028] (1) Acid washing-saturated sodium chloride washing-water washing method: Weigh 50 mg of the crude product of P188-CHMC from which CHM has been removed in a vial, add distilled water, extract with DCM, and then use 100 mmol L -1 Wash 3 times with hydrochloric acid, saturated sodium chloride and ice water...

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 belongs to the field of a high-molecular material, and specifically relates to a DMAP removal method for synthesis of multiple cholesterol-grafted amphiphilic high-molecular materials. The method specifically comprises: (1) dissolving a cholesterol-grafted amphiphilic high-molecular material in toluene, heating the obtained product to 25-100 DEG C, and performing ultrasonic treatmentto dissolve the cholesterol-grafted amphiphilic high-molecular material; (2) performing centrifugation with the rotating speed being 1000-15000 rpm to separate a DMAP-cholesterol intermediate from the toluene solution of the cholesterol-grafted amphiphilic high-molecular material; and (3) taking the toluene solution layer out, and performing pressure reduction to remove toluene, thereby obtainingthe pure cholesterol-grafted amphiphilic high-molecular material. The method has the advantages that (1) the method can be used to remove DMAP from multiple cholesterol-grafted amphiphilic high-molecular materials; and (2) the toluene precipitation method is simple to operate, high in purification efficiency, controllable in result, and beneficial for industrial production.

Description

technical field [0001] The invention belongs to the field of macromolecular materials, and in particular relates to a method for removing DMAP in the synthesis of various grafted cholesterol amphiphilic macromolecular materials. Background technique [0002] 4-Dimethylaminopyridine (4-Dimethylaminopyridine, DMAP) is a high-efficiency catalyst in chemical synthesis, which can be used to improve the speed and yield of various acylation reactions, such as acid chlorides, acid anhydrides, carboxylic acids, etc. Ester-forming reaction, amidation reaction with amines (STEGLICHW, H FLE G.4-Dimethylamino-pyridin, ein hochwirksamer Acylierungskatalysator. Angewandte Chemie, 1969,81(23):1001-1001.) (SCRIVEN EF.4-Dialkylaminopyridines: super acylation and alkylation catalysts. Chemical Society Reviews, 1983, 12(2):129-161.). Taking the reaction of acid anhydride and alcohol to form an ester as an example, the catalytic mechanism of DMAP is that the 4-position nitrogen atom on the pyri...

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): C08G65/30
Inventor 邓意辉田清菁宋艳志苏钰清李博群全晶晶王旭玲
Owner SHENYANG PHARMA UNIVERSITY
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com