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A kind of preparation method of m-peg polymer

A technology for polymers and products, applied in the field of preparation of m-PEG polymers, can solve the problems of difficult product purification, many synthesis steps, cumbersome operations, etc., and achieve the effects of reducing purification difficulty, low environmental pollution, and low energy consumption

Active Publication Date: 2018-07-06
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] 1) There are many synthetic steps, the yield is low, and product purification is difficult;
[0010] 2) There is currently no report on the m-PEG synthesis route above 2500da. The longest m-PEG chain is 2484da developed by the recently reported Livingston team. 4000da is the minimum requirement for the PEG series to have a recessive effect in biopharmaceuticals;
[0011] 3) PEG monofunctionalization requires a large excess of PEG (up to 10eq), as well as expensive reagents and cumbersome operations

Method used

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  • A kind of preparation method of m-peg polymer
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  • A kind of preparation method of m-peg polymer

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Embodiment 1

[0051] (1) Add 80mL of triethylene glycol monomethyl ether and 104mL of triethylamine to 300mL of dichloromethane, stir, weigh 114.4g of p-toluenesulfonyl chloride, dissolve with 300mL of dichloromethane, and add dropwise to In the reaction system, the reaction was completed at room temperature for 10 hours. TLC (PE:EA=1:1) showed that the reaction was over, the raw materials disappeared, the insoluble solids were removed by filtration, washed with saturated sodium bicarbonate, extracted with dichloromethane, and separated and purified by column chromatography to obtain 137.2g of the sulfonylated product (yellow liquid, Yield: 86%). NMR spectrum such as figure 1 with figure 2 As shown, the nuclear magnetic data is as follows: 1 H NMR(400MHz, CDCl 3 ): δ: 7.755 (d, J = 4.0 Hz, 2H); 7.307 (d, J = 4.0 Hz, 2H); 4.131 ~ 4.107 (m, 2H); 3.656 ~ 3.632 (m, 2H); 3.580 ~ 3.549 ( m, 6H); 3.499~3.477 (m, 2H); 3.328 (s, 3H); 2.407 (s, 3H); 13 C NMR(100MHz, CDCl 3 ): δ: 144.670; 132.821; 12...

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Abstract

The invention discloses a method for preparing m-PEG. The preparation method uses triethylene glycol monomethyl ether and tetraethylene glycol as raw materials, undergoes a sulfonylation reaction to obtain a sulfonylated product, and then uses sodium hydride to obtain a sulfonylated product. Obtain m-PEG crude product, react with benzoyl chloride to obtain benzoyl-protected product, and finally deprotect under alkaline conditions to obtain m-PEG pure product. In the preparation method, the m-PEG crude product is benzoylated, so that the product has UV absorption, which is convenient for column chromatography separation and purification, and finally deprotected to obtain m-PEG, which greatly reduces the difficulty of product purification and improves the purity of the product , in line with the quality requirements of the pharmaceutical field.

Description

Technical field [0001] The invention belongs to the field of medicine synthesis, and specifically relates to a preparation method of m-PEG polymer. Background technique [0002] Polyethylene glycol (PEG) is a type of low molecular weight water-soluble polyether obtained by the gradual addition polymerization of ethylene oxide and water or ethylene glycol. Polyethylene glycol monomethyl ether (m-PEG) is a polymer formed after one end of the hydroxyl group of polyethylene glycol is replaced by a methoxy group. One end is a methoxy group and one end is a hydroxyl group. The molecular formula is CH 3 O—(CH 2 CH 2 O) n —H. Its properties are relatively stable, with lubricity and hygroscopicity, most of which are easily soluble in water, soluble in organic solvents such as methylene chloride, tetrahydrofuran, ethanol, and almost insoluble in ether. Polyethylene glycol monomethyl ether with a molecular weight below 1000 is usually a colorless, transparent, clear and viscous liquid at r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/13C07C41/26
CPCC07C41/01C07C41/26C07C67/14C07C303/28C07C43/135C07C69/78C07C43/13C07C309/73
Inventor 任红军陈铮凯董卫朋
Owner ZHEJIANG SCI-TECH UNIV