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Preparation method of mPEG-amine

A technology of polyethylene glycol amine and monomethoxy, which is applied in the field of organic chemistry, can solve the problems of difficult industrial production and cumbersome operation, and achieve the effects of easy industrial production, simple post-processing and less by-products

Active Publication Date: 2018-06-01
EAST CHINA NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using monomethoxypolyethylene glycol as the starting material, the target product monomethoxypolyethylene glycol amine (Ⅲ) is obtained through Gabriel reaction. This synthetic route needs to purify the reaction intermediate by column chromatography, and the operation is relatively cumbersome , it is difficult to produce industrially

Method used

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  • Preparation method of mPEG-amine
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  • Preparation method of mPEG-amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1.1 Preparation of compound monomethoxy polyethylene glycol azide 2000

[0039] Under the protection of nitrogen, 2.0 g of monomethoxy polyethylene glycol 2000 and 0.53 g of triphenylphosphine were added. Dissolve 0.56g of diphenylphosphoryl azide in 12mL of dry dichloromethane, place the reaction bottle in a low temperature environment of 0°C and stir for a certain period of time until the temperature in the reaction bottle is lower than 5°C, then slowly add azo 0.4 g of diisopropyl diformate, keep the temperature below 15°C during the dropwise addition. After the dropwise addition, the reaction system gradually changed from cloudy to clear, and the color changed from light yellow to golden yellow. After 3 hours of reaction, the reaction was complete, and the volume was evaporated to dryness under reduced pressure to obtain a yellow oil, which was purified by beating with anhydrous ether to obtain 1.72 g of the product with a yield of 84.13%.

[0040] 1H-NMR (CDCl 3...

Embodiment 2

[0067] 2.1 Preparation of compound monomethoxy polyethylene glycol amine 2000

[0068] Dissolve 2 g of monomethoxypolyethylene glycol azide 2000 in 20 mL of dry tetrahydrofuran, then add 0.2 g of 10% palladium carbon, replace the air in the reaction bottle with hydrogen, and react at 25°C for 24 hours, and the reaction is complete. The palladium carbon was removed by suction filtration, the solvent was evaporated to dryness under reduced pressure, and purified by beating with anhydrous diethyl ether to obtain 1.8 g of the product with a yield of 90.14%.

[0069] H-NMR (400M) δ = 3.65 (3H, s), 3.38 (93H, J = 8Hz, d)

[0070] MS(EI):m / e=2016.5

[0071] 2.2 Preparation of compound monomethoxy polyethylene glycol amine 2000

[0072] Dissolve 2 g of monomethoxypolyethylene glycol azide 2000 in 20 mL of dry tetrahydrofuran, then add 0.2 g of 5% palladium on carbon, replace the air in the reaction bottle with hydrogen, and react at 25°C for 24 hours, and the reaction is complete. ...

Embodiment 3

[0088] Preparation of Compound Monomethoxypolyethylene Glycol Azide 1000

[0089] Under the protection of nitrogen, 1.0 g of monomethoxy polyethylene glycol 1000 and 0.53 g of triphenylphosphine were added. Dissolve 0.56g of diphenylphosphoryl azide in 10mL of dry dichloromethane, place the reaction bottle in a low temperature environment of 0°C and stir for a certain period of time until the temperature in the reaction bottle is lower than 5°C, then slowly add azo 0.4 g of diisopropyl diformate, keep the temperature below 15°C during the dropwise addition. After the dropwise addition, the reaction system gradually changed from cloudy to clear, and the color changed from light yellow to golden yellow. After 3 hours of reaction, the reaction was complete, and the volume was evaporated to dryness under reduced pressure to obtain a yellow oil, which was purified by beating with anhydrous ether to obtain 0.86 g of the product with a yield of 83.25%.

[0090] 1H-NMR (CDCl3, 400M)...

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Abstract

The invention discloses a preparation method of mPEG-amine and belongs to the field of chemical synthesis. A compound shown in the formula (1), namely, mPEG serving as an initial material and DPPA (diphenylphosphoryl azide) are subjected to a Mitsunobu substitution reaction in a first solvent under the action of triphenyl phosphine and a catalyst, a product and hydrogen are subjected to a reduction reaction, and the target compound mPEG-amine is obtained. The target compound mPEG-amine can be obtained through two-step synthesis with the method, and the method has controllable conditions, simple aftertreatment, few side reactions and high yield and meets the requirement of industrial production.

Description

technical field [0001] The invention belongs to chemical synthesis in the field of organic chemistry, and in particular relates to a preparation method of monomethoxy polyethylene glycol amine. Background technique [0002] Modified PEG, also known as modified polyethylene glycol, is PEG modified with chemical modification groups or biologically active groups. In drug development research, in order to increase the half-life of protein or polypeptide drugs in vivo, reduce immunogenicity, and increase the water solubility of drugs, the activated polyethylene glycol is chemically coupled to proteins, polypeptides, small molecule organic drugs and on liposomes. After the drug is modified by PEG, it often has the following advantages: 1. Longer half-life; 2. Lower maximum blood drug concentration; 3. Less fluctuation in blood drug concentration; 4. Less enzymatic degradation; Less immunogenicity and antigenicity; 6. Less toxicity; 7. Better solubility; 8. Reduced frequency of m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/335C08G65/322
CPCC08G65/322C08G65/3356
Inventor 罗宇王思洋徐运楠占莉周朴康立涛李倩
Owner EAST CHINA NORMAL UNIV
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