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Method for synthesizing alpha-quaternary carbon amino acid

A synthetic method and amino acid technology, applied in the field of synthesis of α-quaternary carbon amino acids, can solve difficult problems such as the synthesis of α-quaternary carbon amino acids

Active Publication Date: 2018-11-06
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, like other methods, this method is difficult to apply to the synthesis of α-quaternary amino acids

Method used

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  • Method for synthesizing alpha-quaternary carbon amino acid
  • Method for synthesizing alpha-quaternary carbon amino acid
  • Method for synthesizing alpha-quaternary carbon amino acid

Examples

Experimental program
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Effect test

Embodiment 1

[0062] To a dry Schlenk tube (10 mL) containing magnetons was added the reaction substrate (0.2 mmol), 4CzIPN (4 mg, 0.004 mmol, 2 mol%). The Schlenk tube was then transferred into the glove box, where it was loaded with Cs 2 CO 3 (294mg, 0.9mmol, 4.5 times equivalent). Remove the Schlenk tube from the glove box and connect to a CO 2 On the double row pipe of the steel cylinder, pump and charge CO on the double row pipe 2 At least 3 times, drain the N in the tube 2 , so that the tube is filled with CO 2 gas. Then in CO 2 Add DMF (2mL) and i PR 2 NEt (100 μL, 3 equiv.). Finally, the reaction solution was placed 2-4 cm away from the 30W blue LED, and stirred at room temperature (25° C.) for 4 hours. The mixture was then quenched with 1 mL of water, 2.5 mL of ethyl acetate and 2 mL of 2N hydrochloric acid, then directly concentrated and spin-dried. The residue was purified by flash column chromatography (first with petroleum ether / ethyl acetate 5 / 1 (v / v) and 0.2-0.3% g...

Embodiment 2

[0070] To a dry Schlenk tube (10 mL) containing magnetons was added the reaction substrate (0.2 mmol), 4CzIPN (2 mg, 0.002 mmol, 1 mol%). The Schlenk tube was then transferred into a glove box, which contained K 2 CO 3 (139 mg, 1.0 mmol, 5 equivalents). Remove the Schlenk tube from the glove box and connect to a CO 2 On the double row pipe of the steel cylinder, pump and charge CO on the double row pipe 2 At least 3 times, drain the N in the tube 2 , so that the tube is filled with CO 2 gas. Then in CO 2 Add DMF (2mL) and i PR 2 NEt (67 μL, 2 equiv). Finally, the solution was placed 2-4cm away from the 30W blue LED, and stirred at room temperature (25°C) for 4 hours. The mixture was then quenched with 1 mL of water, 2.5 mL of ethyl acetate and 2 mL of 2N hydrochloric acid, then directly concentrated and spin-dried. The residue was purified by flash column chromatography (first with petroleum ether / ethyl acetate 5 / 1 (v / v) and 0.2-0.3% glacial acetic acid, then with p...

Embodiment 3

[0072] To a dry Schlenk tube (10 mL) containing magnetons was added the reaction substrate (0.2 mmol), 4CzIPN (10 mg, 0.01 mmol, 5 mol%). The Schlenk tube was then transferred into a glove box, where it was filled with Na 2 CO 3 (106mg, 1.0mmol, 5 times equivalent). Remove the Schlenk tube from the glove box and connect to a CO 2 On the double row pipe of the steel cylinder, pump and charge CO on the double row pipe 2 At least 3 times, drain the N in the tube 2 , so that the tube is filled with CO 2 gas. Then in CO 2 Add DMF (2mL) and i PR 2 NEt (167 μL, 5 equivalents). Finally, the solution was placed 2-4 cm away from the 30W blue LED, and stirred at room temperature (25° C.) for 4 hours. The mixture was then quenched with 1 mL of water, 2.5 mL of ethyl acetate and 2 mL of 2N hydrochloric acid, then directly concentrated and spin-dried. The residue was purified by flash column chromatography (first with petroleum ether / ethyl acetate 5 / 1 (v / v) and 0.2-0.3% glacial a...

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Abstract

The invention provides a method for synthesizing an alpha-quaternary carbon amino acid. The method is characterized by comprising the following steps: putting a substrate, a photocatalyst and an alkali into a dry reaction tube, adding a reducing agent and a solvent in a CO2 atmosphere, carrying out a reaction under radiation of visible light, after the raw material reaction is completed, carryingout quenching treatment on a mixture after the reaction, and carrying out separation and purification, thereby obtaining the alpha-quaternary carbon amino acid, wherein the photocatalyst comprises 4CzIPN or Ir[(ppy)2(dtbppy)]PF6; the reaction substrate comprises an acrylamide compound or an imine compound. By adopting the method, the alpha-quaternary carbon amino acid can be efficiently synthesized under visible light induction in the presence of CO2; the scheme of the invention is gentle in reaction condition and wide in reaction substrate selectivity, the reaction can be amplified to a gram-grade scale, and the yield is barely affected; by adopting the method, the defects that the prior art is high in reagent toxicity and harsh in reaction condition, and good industrial application prospects can be achieved.

Description

technical field [0001] The invention belongs to the field of amino acid synthesis, and in particular relates to a synthesis method of α-quaternary carbon amino acid. Background technique [0002] As we all know, α-amino acid (α-AA) is the key structural unit of polypeptides, proteins and natural products, and plays a vital role in biochemistry, organic chemistry and even life. Therefore, the synthesis of α-amino acids has always been a very important field. Among the various methods for the synthesis of unnatural α-amino acids, readily available organic compounds such as imines, enamides and CO 2 The carboxylation of ) has aroused widespread interest among chemists due to its low cost and simple scheme. Sato, Zhang, Jamison et al. have made significant contributions to this field and obtained synthetic strategies for different α-amino acid derivatives. However, these strategies have obvious disadvantages, such as the need to use toxic and relatively expensive bimetallic re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/87C07C233/63C07C233/47C07C233/51C07C233/49C07C235/52C07C231/12C07B41/08C07D333/38C07D307/68
CPCC07B41/08C07C231/12C07D307/68C07D333/38C07C2601/02C07C2601/14C07C233/87C07C233/63C07C233/47C07C233/51C07C233/49C07C235/52
Inventor 余达刚李静鞠涛付强叶剑衡张振廖黎丽颜思顺田兴洋罗书平
Owner SICHUAN UNIV
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