A kind of synthetic method of α-amino acid derivatives

A synthetic method and technology of amino acids, applied in the field of organic synthesis methodology, can solve the problems of unreported disconnection of carbon-nitrogen double bonds, etc., and achieve the effect of simple reaction conditions and high reaction yield

Active Publication Date: 2020-11-17
NANJING TECH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Scientists have also done a lot of research on the ring-opening reaction of aziridine compounds, including the breaking of the carbon-nitrogen single bond and the breaking of the carbon-carbon single bond, but there are almost no reports in the literature on the breaking of the carbon-nitrogen double bond.

Method used

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  • A kind of synthetic method of α-amino acid derivatives
  • A kind of synthetic method of α-amino acid derivatives
  • A kind of synthetic method of α-amino acid derivatives

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Experimental program
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Embodiment 1

[0023] The reaction formula of the whole process is as follows:

[0024]

[0025]

[0026] The preparation method of the aziridine compound with amide: add 1.0 equiv. (0.2 mmol) of the oxazole ring to the Shrek tube, add 2 mL of analytical pure ethanol, 1% equiv. of ruthenium catalyst, under the condition of green light Under reaction for 24-72 hours. After the reaction, spin off the solvent with a rotary evaporator, extract the organic phase three times with water and dichloromethane, dry the organic phase with anhydrous sodium sulfate, spin off the excess solvent, and then pass through column chromatography (dichloromethane / methanol) to obtain Aziridines with amides.

[0027] Synthesis of α-amino acid derivatives (diphenylthiopropionamide compound): add 1.0 equiv. (0.2 mmol) of the above-mentioned aziridine compound with amide to the Shrek tube, 1.5 mL of analytically pure methanol, and 1.5 mL of pH 7.40 buffer solution (potassium dihydrogen phosphate-dipotassium hyd...

Embodiment 2

[0029] The reaction formula of the whole process is as follows:

[0030]

[0031] The preparation method of the aziridine compound with ester group: add 1.0equiv (0.2mmol) of p-toluenesulfonimide derivative to the Shrek tube, add 2mL of analytically pure dichloromethane, 1.5equiv (0.3mmol) Triethylamine was stirred and reacted in an ice-water bath for 6 hours, and the reaction stopped when the temperature returned to room temperature. Extract the organic phase with water and dichloromethane three times, dry the organic phase with anhydrous sodium sulfate, spin off more than the solvent, and then pass through column chromatography (petroleum ether / ethyl acetate) to obtain the aziridine compound with ester group .

[0032] Synthesis of α-amino acid compounds (diphenylthiopropylamine tert-butyl ester compound): Add 1.0equiv (0.2mmol) of the above-mentioned aziridine compound with ester group to the Shrek tube, 1.5mL analytical pure methanol, 1.5mLpH The buffer solution (pota...

Embodiment 3

[0034] The reaction formula of the whole process is as follows:

[0035]

[0036] The preparation method of 3-phenylaziridine compound: add 1.0 equiv (0.2 mmol) of 1-azidovinylbenzene derivative to a round bottom flask, add 10 mL of toluene, and heat at reflux at 110 ° C for 6 hours . After the reaction is finished, spin off the excess solvent, and then go through column chromatography (petroleum ether / ethyl acetate) to obtain the 3-phenylaziridine compound.

[0037] Synthesis of α-amino acid compounds (diphenylthiopropylamine compound): Add 1.0 equiv (0.2 mmol) of the above-mentioned 3-phenylazacyclopropene compound to the Shrek tube, 1.5 mL of analytically pure methanol, and 1.5 mL of pH value is 7.40 The buffer solution (potassium dihydrogen phosphate-dipotassium hydrogen phosphate) was vacuumized, and 8.0 equiv of thiophenol was added dropwise to the Shrek tube to react for 20 hours under the condition of blowing nitrogen. After the reaction was completed, the reactio...

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Abstract

Disclosed is a method of synthesizing an α-amino acid derivative, where an azirine compound, used as raw material, is reacted with a sulfhydryl compound in a mixed system of an organic solvent and a buffer solution under the protection of nitrogen to produce the α-amino acid derivative. In the reaction, the carbon-nitrogen double bond of the azirine compound is attacked by the sulfhydryl compound, so that the azirine compound is directly opened to form the α-amino acid derivative of which the same carbon atom is added with two molecules of the sulfhydryl compound. This method can be performed directly in an aqueous phase without using a metal catalyst.

Description

technical field [0001] The invention relates to a synthesis method of α-amino acid derivatives, belonging to the technical field of organic synthesis methodology. Background technique [0002] α-amino acid is the main component of protein, the most important amino acid in organisms, and one of the most important and versatile building blocks for biological and chemical synthesis. At present, although there are now a series of methods for the total synthesis of amino acids, such as the alkylation of enamide and α-enantioselectively hydrogenated glycine synthons for αAA synthesis, or the application of aromatic aldehydes with CCl 2- In the presence of phase transfer catalysts, aromatic aldehydes react with chloroform, potassium hydroxide, carp chloride and ammonia to further obtain α-amino acids. However, these methods often have many reaction steps and a long reaction cycle, and the α-amino acid can only be synthesized under the condition of adding a metal catalyst in a comp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/18C07C323/60C07C323/58C07C323/29C07D203/04
CPCC07B2200/07C07C319/18C07D203/04C07C323/60C07C323/58C07C323/29C07C323/63C07C319/06
Inventor 姜耀甲陈阳罗德平
Owner NANJING TECH UNIV
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