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Method for electrochemical synthesis of non-natural amino acid derivatives

An unnatural amino acid and electrochemical technology, which is applied in the field of electrochemical synthesis of unnatural amino acid derivatives, can solve problems such as high temperature, and achieve the effects of high total yield, wide substrate applicability, and mild reaction conditions

Pending Publication Date: 2021-11-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problem of high temperature and excessive oxidizing agent required by the synthesis method in the prior art, the present invention provides a method for synthesizing unnatural amino acid under electrochemical conditions with N-aryl glycine ester and redox active ester

Method used

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  • Method for electrochemical synthesis of non-natural amino acid derivatives
  • Method for electrochemical synthesis of non-natural amino acid derivatives
  • Method for electrochemical synthesis of non-natural amino acid derivatives

Examples

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Embodiment 1

[0031]

[0032] 2-(p-Toluidyl) ethyl acetate (58mg, 0.3mmol), cyclohexyl redox active ester CAS: 126812-30-4 (123mg, 0.45mmol), lithium perchlorate (106mg, 1.0mmol), Nickel chloride hexahydrate (7mg, 0.03mmol), 4,4'-di-tert-butyl-2,2'-bipyridine (9mg, 0.033mmol), ferrocene (11mg, 0.06mmol), triethylenediamine (74mg, 0.66mmol) was dissolved in 6mL dimethyl sulfoxide to obtain an electrolyte solution, with a carbon felt electrode as an anode and a nickel foam electrode as a cathode, turn on the power supply under nitrogen protection, magnetically stir at room temperature, and set the current to 8mA ( 3-5V), after TLC monitors that the reaction is complete, stop powering on. The mixture was washed with water and extracted with ethyl acetate (3×20 mL), the organic solutions were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure, and purified by silica gel column chromatography using petroleum ether:ethyl acetate (150:1) as eluent , collected...

Embodiment 2

[0034] According to the method described in Example 1, the difference is that no catalyst, ligand, and additive are added, and the solvent is replaced by N,N-dimethylformamide (6 mL) for dimethyl sulfoxide to obtain 12 mg of product with a yield of 14 %, the product is a colorless liquid. R f =0.3(PE:EA=30:1)

Embodiment 3

[0036] According to the method described in Example 1, the difference is that no additives are added, and the solvent is replaced by N,N-dimethylformamide (6mL) for dimethyl sulfoxide to obtain 45mg of the product with a yield of 55%. colored liquid. R f =0.3(PE:EA=30:1).

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Abstract

The invention provides a method for synthesizing non-natural amino acid from N-aryl glycine ester and redox active ester under electrochemical conditions. The method is mild in reaction condition, wide in substrate applicability, easy to obtain the raw materials N-aryl glycine ester compound and redox active ester, free of multi-step preparation of the substrate and high in total yield. According to the innovation, active carboxylic ester is electrochemically decarboxylated and then reacts with an N-aryl glycine ester compound in one step to obtain the unnatural amino acid derivative; and the highest yield of the obtained non-natural amino acid derivative is 80%.

Description

(1) Technical field [0001] The invention relates to a method for electrochemically synthesizing unnatural amino acid derivatives, in particular to a method for preparing unnatural amino acid derivatives in one step from N-aryl glycine ester and active carboxylate under electrochemical conditions. (2) Background technology [0002] Amino acids widely exist in natural products and drug molecules, and play an extremely important role in human life. Unnatural amino acids derived from the natural environment or synthesized by chemists have received extensive attention due to their structures and applications. Unnatural amino acids not only play an important role in asymmetric synthesis, but also have a wide range of applications in the preparation of biologically active peptides, which can significantly improve pharmacokinetic properties. In recent years, with the approval of amino acid drugs and peptide biological agents, the development of new α-amino acid compounds has been f...

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Application Information

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IPC IPC(8): C25B3/09C25B3/20
CPCC25B3/09C25B3/20
Inventor 张逢质陈娜
Owner ZHEJIANG UNIV OF TECH