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Preparation method of m-PEG (m-polyethylene glycol) polymer

A technology for polymers and products, applied in the field of m-PEG polymer preparation, 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: 2016-07-06
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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  • Preparation method of m-PEG (m-polyethylene glycol) polymer
  • Preparation method of m-PEG (m-polyethylene glycol) polymer
  • Preparation method of m-PEG (m-polyethylene glycol) polymer

Examples

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Embodiment 1

[0051] (1) Add 80mL of triethylene glycol monomethyl ether and 104mL of triethylamine into 300mL of dichloromethane, stir, weigh 114.4g of p-toluenesulfonyl chloride, dissolve it in 300mL of dichloromethane, and add it dropwise to In the reaction system, the dropwise reaction was completed at room temperature for 10 hours. TLC (PE: EA = 1: 1) showed that the reaction was complete and the raw materials disappeared. The insoluble solid was removed by filtration, washed with saturated sodium bicarbonate, extracted with dichloromethane, separated and purified by column chromatography to obtain 137.2 g of sulfonylated product (yellow liquid, Yield: 86%). NMR spectrum such as figure 1 and figure 2 As shown, the NMR data are as follows: 1 HNMR (400MHz, CDCl 3 ): δ: 7.755(d, J=4.0Hz, 2H); 7.307(d, J=4.0Hz, 2H); 4.131~4.107(m, 2H); 3.657~3.632(m, 2H); 3.580~3.549( m, 6H); 3.499~3.477(m, 2H); 3.328(s, 3H); 2.407(s, 3H); 13 CNMR (100MHz, CDCl 3 ): δ: 144.670; 132.821; 129.682; 12...

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Abstract

The invention discloses a preparation method of m-PEG (m-polyethylene glycol). The preparation method comprises the following steps: by using triglycol monomethyl ether and tetraethylene glycol as raw materials, carrying out sulfonylation reaction to obtain a sulfonylation product, reacting under the action of sodium hydride to obtain an m-PEG crude product, carrying out reaction on the m-PEG crude product and benzoyl chloride to obtain a benzoyl protected product, and finally, carrying out deprotection under alkaline conditions to obtain the m-PEG pure product. In the preparation method, the m-PEG crude product is benzoylated, so that the product can absorb UV, and is convenient for separation and purification by column chromatography; and finally, the deprotection is performed to obtain the m-PEG, thereby greatly lowering the product purification difficulty, enhancing the product purity and satisfying the quality requirements in the field of drugs.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a preparation method of m-PEG polymer. Background technique [0002] Polyethylene glycol (PEG) is a kind of water-soluble polyether with low molecular weight obtained by the gradual addition polymerization of ethylene oxide and water or ethylene glycol. Polyethylene glycol monomethyl ether (m-PEG) is a polymer formed by substituting one terminal hydroxyl group of polyethylene glycol with a methoxy group. The molecular formula is CH 3 O—(CH 2 CH 2 O) n —H. It is relatively stable in nature, has lubricity and hygroscopicity, and most of it is 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 viscous liquid with low viscosity at room temperature; polyethylene glycol monom...

Claims

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Application Information

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Patent Type & Authority Applications(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