Synthetic method of α-amino acid derivatives substituted by α-alkyl branched chain

A synthesis method and amino acid technology are applied in the field of synthesis of α-amino acid derivatives, which can solve the problems of few optional species, high difficulty in preparing reagents, harsh storage conditions, etc., and achieve simple and feasible operation process, non-toxic raw materials, and method. easy effect

Inactive Publication Date: 2017-01-25
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Synthetic method of α-amino acid derivatives substituted by α-alkyl branched chain
  • Synthetic method of α-amino acid derivatives substituted by α-alkyl branched chain
  • Synthetic method of α-amino acid derivatives substituted by α-alkyl branched chain

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 method of synthesizing an α-amino acid derivative with α-alkyl side chain substitution. The method comprises: reacting an alkene with 9-bbn at 0-80˚C for 0.5-12 h, and then adding an imine to react at 0-90˚C for 12-48 h with the presence of a transition metal salt, a base and an organic solvent to generate an α-amino acid derivative. In the present invention, an alkene is employed to in-situ generate an alkyl boron reagent, wherein the reaction condition is mild and the alkaline can be selected from a wide range. For the existing synthesis methods, a strict anhydrous and anaerobic condition is required, complex reaction operations are involved, and a low temperate is needed for the reaction to occur, thus causing a high cooling cost. On the contrary, the present invention does not require an anhydrous and anaerobic condition, and the reaction can occur at the room temperature or 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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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/10C07C229/36C07C229/18C07C229/28C07D333/24
CPCC07C227/10C07C229/18C07C229/28C07C229/36C07C333/24
Inventor 曾伟黄房生肖新生卢晓霞
Owner SOUTH CHINA UNIV OF TECH
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