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Cysteine derivative and synthesis method thereof

A technology of cysteine ​​and a synthetic method, applied in the field of amino acid and preparation thereof, can solve the problems of expensive mass production and use of metal palladium, unpleasant smell of thiol, expensive reaction raw materials, etc., and achieves low cost, high yield, and method. Simple and easy effects

Active Publication Date: 2020-12-04
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But metal palladium is too expensive to be used in mass production
There are also some methods that use aminoalcohols to react with mercaptans. In this method, the smell of mercaptans is too unpleasant, and the price of aminoalcohols is much higher than that of cysteine.
[0004] In summary, the current methods have great defects, especially the reaction raw materials are too expensive and the reaction operation is too complicated in the current synthesis method of cysteine ​​derivatives.

Method used

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  • Cysteine derivative and synthesis method thereof
  • Cysteine derivative and synthesis method thereof
  • Cysteine derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] In this example, product 1 was synthesized with N-benzyloxycarbyl-protected cysteine ​​and methyl p-bromobenzoate as raw materials, and its structural formula is:

[0028]

[0029] In this embodiment, a synthetic method of cysteine ​​derivatives, the steps are as follows:

[0030] To a dry Schlenk tube, add N-benzyloxycarbyl-protected cysteine ​​(0.03mmol, 80.7mg, 100mol%), methyl p-bromobenzoate (0.032mmol, 68.8mg, 110mol%), zinc powder (0.06 mmol, 39mg, 200mol%), anhydrous magnesium chloride (0.03mmol, 28.6mg, 100mol%), Ni(acac) 2 (0.003mmol, 7.7mg, 10mol%), 4-dimethoxybipyridine (0.0045mmol, 0.0148g, 15mol%), and finally DMSO1ml was added by syringe, and stirred at room temperature for 8-12h. After the reaction, the colorless liquid 1 can be obtained by directly separating by column chromatography (ethyl acetate:petroleum ether=2:8) without post-treatment, and the yield is 90-95%.

[0031] The product 1 synthesized by the method of this embodiment is characteriz...

Embodiment 2

[0035] This embodiment is basically the same as Embodiment 1, especially in that:

[0036] In this example, product 2 was synthesized using N-benzyloxycarbonyl-protected cysteine ​​and 4-trifluoromethylbromobenzene as raw materials, and its structural formula is:

[0037]

[0038] In this embodiment, a synthetic method of cysteine ​​derivatives, the steps are as follows:

[0039] To a dry Schlenk tube, add N-benzyloxycarbyl-protected cysteine ​​(0.03mmol, 80.7mg, 100mol%), 4-trifluoromethylbromobenzene (0.032mmol, 72mg, 110mol%) zinc powder ( 0.06mmol, 39mg, 200mol%), anhydrous magnesium chloride (0.03mmol, 28.6mg, 100mol%), Ni(acac) 2 (0.003mmol, 7.7mg, 10mol%), 4-dimethoxybipyridine (0.0045mmol, 0.0148g, 15mol%), and finally DMSO1ml was added by syringe, and stirred at room temperature for 8-12h. After the reaction, the yellow solid 2 can be obtained directly by column chromatography (ethyl acetate:petroleum ether=2:8) without post-treatment, and the yield is 83-88%.

...

Embodiment 3

[0044] This embodiment is basically the same as the previous embodiment, and the special features are:

[0045] In this example, product 3 was synthesized with N-benzyloxycarbonyl-protected cysteine ​​and 4-bromobenzaldehyde as raw materials, and its structural formula is:

[0046]

[0047]In this embodiment, a synthetic method of cysteine ​​derivatives, the steps are as follows:

[0048] To a dry Schlenk tube, add N-benzyloxycarbonyl-protected cysteine ​​(0.03mmol, 80.7mg, 100mol%), 4-bromobenzaldehyde (0.032mmol, 59.2mg, 110mol%), zinc powder (0.06mmol , 39mg, 200mol%), anhydrous magnesium chloride (0.03mmol, 28.6mg, 100mol%), Ni(acac) 2 (0.003mmol, 7.7mg, 10mol%), 4-dimethoxybipyridine (0.0045mmol, 0.0148g, 15mol%), and finally DMSO 1ml was added by syringe, and stirred at room temperature for 8-12h. After the reaction, the white solid 3 can be obtained by direct column chromatography (ethyl acetate:petroleum ether=2:8) without post-treatment, and the yield is 70-75%. ...

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Abstract

The invention discloses a cysteine derivative and a synthetic method thereof. According to the method disclosed by the invention, cysteine ester and aryl bromide are used as substrates, and under theaction of a catalyst, a ligand, a reducing agent and an additive, a mild reaction is carried out for 6-12 hours at normal temperature to obtain the cysteine derivative. The method provided by the invention has the advantages of cheap catalyst metal, simple and easily available raw materials, mild reaction, one-step reaction, simple steps, safe operation and high yield.

Description

technical field [0001] The invention relates to an amino acid and a preparation method thereof, in particular to a cysteine ​​and its derivatives and a preparation method thereof, which are applied in the technical field of amino acid and its preparation technology. Background technique [0002] Cysteine ​​is one of the essential amino acids in the human body and has an irreplaceable position in the human body. Such cysteine ​​derivatives have potential biological activity and may have potential medical value. [0003] At present, there are some common synthetic methods that use halogenated aromatic compounds and cysteine ​​to generate the target product under the catalysis of palladium. But metal palladium is too expensive to be used in mass production. There are also some methods to react with aminoalcohols and mercaptans. In this method, the smell of mercaptans is too unpleasant, and the price of aminoalcohols is much higher than that of cysteine. [0004] To sum up, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C323/59C07C323/62C07D215/36C07D217/22
CPCC07C319/14C07C323/59C07C323/62C07D215/36C07D217/22Y02P20/55
Inventor 龚宇昕龚和贵雷川虎童玮琦钱群
Owner SHANGHAI UNIV