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Alpha-aryl substituted amino acid derivative preparation method

An amino acid and derivative technology, applied in the field of compound preparation, achieves the effects of mild reaction conditions, simple reaction and post-processing purification process, high selectivity and high yield

Inactive Publication Date: 2018-09-25
XIAN GERUIDE NEW CHEM MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, direct aryl substitution of oxazolidinones and subsequent synthesis of amino acids with different aryl substitutions have not been reported in the literature.

Method used

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  • Alpha-aryl substituted amino acid derivative preparation method
  • Alpha-aryl substituted amino acid derivative preparation method
  • Alpha-aryl substituted amino acid derivative preparation method

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Experimental program
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Effect test

Embodiment 1

[0020] Under an inert gas atmosphere, 0.261 grams (1 mmol) of oxazolidinone compounds (wherein R1 = methyl, R2 = benzoyl, R3 = tert-butyl) were dissolved in 10 ml of tetrahydrofuran at -78 ° C, and 0.183 g (1.1 mmol) lithium hexamethylsilylamide, stirred and reacted for half an hour, then added 0.172 g (1.1 mmol) bromobenzene, reacted at -78°C for 2 hours, then slowly warmed up to room temperature, and reacted for 12 hours. 5 mL of saturated ammonium chloride solution was added, the mixture was extracted with ethyl acetate (3×10 mL), the combined extracts were dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the crude product was dissolved in 10 ml of 2M trifluoroacetic acid methanol solution, sealed and heated at 130°C for 48 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure, 50 ml of dichloromethane was added, and the organic phase was washed with water (3×10 ml) and dried over anhydrous ...

Embodiment 2

[0022] Under an inert atmosphere, 0.337 grams (1 mmol) of oxazolidinone compounds (wherein R1 = benzyl, R2 = benzoyl, R3 = tert-butyl) were dissolved in 10 ml of toluene at -78 ° C, and 0.219 g (1.1mmol) potassium hexamethylsilylamide, stirred for half an hour, then added 0.249 grams (1.1mmol) of phenyl trifluoromethanesulfonate, reacted at -78°C for 2 hours, then slowly warmed up to room temperature, reaction 12 Hour. 5 mL of saturated ammonium chloride solution was added, the mixture was extracted with ethyl acetate (3×10 mL), the combined extracts were dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the crude product was dissolved in 10 ml of 2M ethanol trifluoroacetic acid solution, sealed and heated at 130°C for 48 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure, 50 ml of dichloromethane was added, and the organic phase was washed with water (3×10 ml) and dried over anhydrous sodium s...

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Abstract

The invention discloses an alpha-aryl substituted amino acid derivative preparation method, which comprises: (1) dissolving an oxazolidinone-based compound in a solvent, adding an alkali, adding an arylating agent, carrying out a reaction for 2 h at a temperature of -78 DEG C, and carrying out a reaction for 12 h at a room temperature to obtain an aryl-substituted oxazolidinone compound; and (2) hydrolyzing the obtained aryl-substituted oxazolidinone compound by using trifluoroacetic acid to obtain the alpha-aryl substituted amino acid derivative. According to the present invention, the alpha-aryl substituted amino acid derivative is synthesized by using the oxazolidinone-based compound as the reaction reagent through the arylating reaction and the hydrolyzing reaction; and the method hascharacteristics of high selectivity, high yield, mild reaction conditions, simple reaction and simple post-treatment purification process.

Description

technical field [0001] The invention relates to the field of compound preparation, in particular to a method for preparing α-aryl substituted amino acid derivatives. Background technique [0002] Amino acid is the most basic substance that constitutes biological proteins and is related to life activities. It is the basic unit of protein molecules in organisms and has a close relationship with biological life activities. It has special physiological functions in organisms and is one of the indispensable nutrients. The presence of amino acids in the human body not only provides important raw materials for protein synthesis, but also provides a material basis for promoting growth, normal metabolism, and maintaining life. Amino acids also play an important role in medicine and can be used as therapeutic drugs and for the synthesis of peptide drugs. Due to the limited number and types of amino acids that exist in nature, the synthesis of unnatural amino acids with different sub...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C233/87
CPCC07C231/12C07D263/26C07C233/87
Inventor 孙蓓林泽欣
Owner XIAN GERUIDE NEW CHEM MATERIALS CO LTD
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