Synthesis method of alpha-aminoacid derivative substituted by alpha-alkyl branch

A synthesis method and amino acid technology, applied in the field of synthesis of α-amino acid derivatives, can solve the problems of high difficulty in reagent preparation, harsh storage conditions, and few optional types, and achieve simple and easy operation process, simple method, and simple steps Effect

Inactive Publication Date: 2015-11-04
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The preparation of the above reagents is difficult, the storage conditions are harsh, and there are few options

Method used

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  • Synthesis method of alpha-aminoacid derivative substituted by alpha-alkyl branch
  • Synthesis method of alpha-aminoacid derivative substituted by alpha-alkyl branch
  • Synthesis method of alpha-aminoacid derivative substituted by alpha-alkyl branch

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A synthetic method for α-amino acid derivatives, comprising the following steps:

[0039] (1) In a sealed tube, add p-methoxyaniline (12.3mg, 0.1mmol), ethyl glyoxylate (10.2mg, 0.1mmol), anhydrous sodium sulfate (71mg, 0.5mmol), dichloromethane ( 2 mL), the mixture was stirred at room temperature for 0.5 h. Then the sodium sulfate was removed by filtration, the filter residue was washed with dichloromethane, and the solvent was spin-dried with dichloromethane to obtain 0.1 mmol of imine.

[0040]

[0041] (2) Add styrene (15.1mg, 0.15mmol), 9-bbn (0.3mL, 0.15mmol, 9-bbn is 0.5mol / L THF solution) and anhydrous toluene in a sealed tube that has been evacuated and filled with nitrogen. 1 mL, the mixture was stirred and reacted at 60°C for 1 h, then stopped heating and cooled to room temperature. Then cesium carbonate (5mg, 0.015mmol), cuprous cyanide (0.9mg, 0.01mmol) and the imine of step (1) were added successively, sealed and reacted at 70°C for 24h. After the re...

Embodiment 2

[0049] A synthetic method for α-amino acid derivatives, comprising the following steps:

[0050] (1) In a sealed tube, add p-chloroaniline (12.7mg, 0.1mmol), ethyl glyoxylate (10.2mg, 0.1mmol), anhydrous sodium sulfate (71mg, 0.5mmol), dichloromethane (2mL) , The mixture was stirred and reacted at room temperature for 0.5h. Then the sodium sulfate was removed by filtration, the filter residue was washed with dichloromethane, and the solvent was spin-dried with dichloromethane to obtain 0.1 mmol of imine.

[0051]

[0052] (2) Add styrene (15.1mg, 0.15mmol), 9-bbn (0.3mL, 0.15mmol, 9-bbn is 0.5mol / L THF solution) and anhydrous toluene in a sealed tube that has been evacuated and filled with nitrogen. 1 mL, the mixture was stirred at 0°C for 1 h, then stopped heating and cooled to room temperature. Then sodium carbonate (1.6mg, 0.015mmol), cuprous iodide (1.9mg, 0.01mmol) and the imine of step (1) were added sequentially, sealed and reacted at 90°C for 24h. After the react...

Embodiment 3

[0060] A synthetic method for α-amino acid derivatives, comprising the following steps:

[0061] (1) In a sealed tube, add p-methoxyaniline (12.3mg, 0.1mmol), ethyl glyoxylate (10.2mg, 0.1mmol), anhydrous sodium sulfate (71mg, 0.5mmol), dichloromethane ( 2 mL), the mixture was stirred at room temperature for 0.5 h. Then the sodium sulfate was removed by filtration, the filter residue was washed with dichloromethane, and the solvent was spin-dried with dichloromethane to obtain 0.1 mmol of imine.

[0062]

[0063] (2) Add p-bromostyrene (27mg, 0.15mmol), 9-bbn (0.3mL, 0.15mmol, 0.5mol / L THF solution of 9-bbn) in a sealed tube that has been evacuated and filled with nitrogen, anhydrous Toluene 1mL, the mixture was stirred and reacted at 80°C for 1h, then the heating was stopped and cooled to room temperature. Then sequentially add NaO t Bu (1.5mg, 0.015mmol), palladium acetate (2.4mg, 0.01mmol), the imine of step (1), sealed and reacted at 0°C for 24h. After the reaction ...

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Abstract

The present invention discloses a synthesis method of an alpha-aminoacid derivative substituted by an alpha-alkyl branch. The method comprises the following steps: olefin reacting with 9-bbn at 0-80 DEG C for 0.5-12 h; then adding imine; in the presence of a transition metal salt, an alkali and an organic solvent, performing reacting at 0-90 DEG C for 12-48 h to produce the alpha-aminoacid derivative. According to the present invention, an alkyl boron reagent is produced in a situ manner by using olefin and 9-bbn, the reaction condition is mild, and a variety of olefin may be selected. In addition, the existing synthesis method needs the strict anhydrous oxygen-free condition, the reaction manipulation is complex, the reaction needs to be performed at a low temperature, and the cooling cost is high. However, according to the method, the anhydrous oxygen-free condition is not needed, and the reaction may be performed at the room temperature or at a slightly higher temperature.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a synthesis method of alpha-amino acid derivatives substituted by alpha-alkyl branched chains. Background technique [0002] Amino acids are not only the basic building blocks of proteins, but their derivatives are also important building blocks for many natural products and drug molecules. Amino acids and their derivatives have important uses in the field of biomedicine, and amino acids are also the synthetic precursors of many catalysts. Therefore, the synthesis methods of α-amino acid derivatives have been widely valued. [0003] The currently reported synthesis methods of α-amino acid derivatives mainly include: first, hydrogenation of imines under certain conditions by reducing reagents to obtain target products. Such as: (1) with H 2 As a reducing agent; (2) using Hantzsch ester as a reducing agent; (3) using other reagents as a reducing agent. [0004] The se...

Claims

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Application Information

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IPC IPC(8): C07C227/10C07C229/36C07C229/18C07C229/28C07D333/24
CPCC07C227/10C07C229/18C07C229/28C07C229/36C07C333/24
Inventor 曾伟肖新生卢晓霞
Owner SOUTH CHINA UNIV OF TECH
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