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Derivative containing alpha-aryl-alpha, beta-diamino acid ester and synthesis method and application thereof

A technology of a diamino acid ester and a synthetic method, applied in the field of synthetic medicine and chemical industry, can solve the problems of difficult large-scale application in industrialization, cumbersome operation and post-processing, limited economic value, etc., and achieves low cost, short reaction route, and preparation. short route effect

Active Publication Date: 2017-06-13
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Afterwards, new synthetic methods were discovered one after another, but these new synthetic methods and routes have disadvantages such as long steps, high cost, long time-consuming, low yield, cumbersome operation and post-processing, etc., and are difficult to be applied on a large scale in industrialization. limited economic value
Therefore, above-mentioned method is all unfavorable for containing α-aryl-α, the application of β-diamino acid ester derivative in organic synthesis and its industrial synthesis

Method used

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  • Derivative containing alpha-aryl-alpha, beta-diamino acid ester and synthesis method and application thereof
  • Derivative containing alpha-aryl-alpha, beta-diamino acid ester and synthesis method and application thereof
  • Derivative containing alpha-aryl-alpha, beta-diamino acid ester and synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108]

[0109] With imine (0.24mmol), rhodium acetate (0.0024mmol) and Molecular sieves (300mg) were mixed in a 10mL single-mouth bottle, the oil pump was used for nitrogen ventilation, and 1mL redistilled CH was added with a 1mL syringe. 2 Cl 2 Solution, prepared as mixed solution A, stirred at room temperature for 10 minutes. Then the aryl diazo compound (0.2mmol) and the amide compound (0.2mmol) were dissolved in 1 mL redistilled CH2 Cl 2 solution, prepared as Solution B. Solution B was added to mixed solution A with a syringe pump within 1 hour at 25°C. Stirring for 3 to 12 hours, the reaction mixture was purified by column chromatography to obtain a pure product, the structure of which was shown in formula (a), which was methyl(2S,3S)-3-(4-nitrophenyl)-3 -((2-Hydroxyphenyl)amino)-2-phenyl-2-propynamide propionic acid methyl ester, the yield is 87%, the dr value is equal to 89:11, and the HPLC purity is 96%. Compound shown in formula (a) 1 H NMR schematic as fi...

Embodiment 2

[0112]

[0113] With imine (0.24mmol), rhodium acetate (0.0024mmol) and Molecular sieves (300mg) were mixed in a 10mL single-mouth bottle, the oil pump was used for nitrogen ventilation, and 1mL redistilled CH was added with a 1mL syringe. 2 Cl 2 Solution, prepared as mixed solution A, stirred at room temperature for 10 minutes. Then the aryl diazo compound (0.2mmol) and the amide compound (0.2mmol) were dissolved in 1 mL redistilled CH 2 Cl 2 solution, prepared as Solution B. Solution B was added to mixed solution A with a syringe pump within 1 hour at 25°C. Stirring for 3 to 12 hours, the reaction mixture was purified by column chromatography to obtain a pure product, the structure of which was shown in formula (b), which was methyl(2S,3S)-3-(2-bromophenyl)-3- Methyl ((2-hydroxyphenyl)amino)-2-phenyl-2-propynamide propionate, yield 54%, dr value equal to 94:6, HPLC purity 95%. Compound shown in formula (b) 1 H NMR schematic as Figure 4 As shown, its 13 C NMR sc...

Embodiment 3

[0116]

[0117] With imine (0.24mmol), rhodium acetate (0.0024mmol) and Molecular sieves (300mg) were mixed in a 10mL single-mouth bottle, the oil pump was used for nitrogen ventilation, and 1mL redistilled CH was added with a 1mL syringe. 2 Cl 2 Solution, prepared as mixed solution A, stirred at room temperature for 10 minutes. Then the aryl diazo compound (0.2mmol) and the amide compound (0.2mmol) were dissolved in 1 mL redistilled CH 2 Cl 2 solution, prepared as Solution B. Solution B was added to mixed solution A with a syringe pump within 1 hour at 25°C. Stirring for 3 to 12 hours, the reaction mixture was purified by column chromatography to obtain a pure product, the structure of which was shown in formula (c), which was methyl (2S,3S)-3-(3-bromophenyl)-3- ((2-Hydroxyphenyl)amino)-2-phenyl-2-propynamide propionic acid methyl ester, the yield was 70%, the dr value was equal to 95:5, and the HPLC purity was 97%. Compound shown in formula (c) 1 H NMR schematic a...

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Abstract

The invention discloses a derivative containing alpha-aryl-alpha, beta-diamino acid ester and a synthesis method thereof. The derivative containing the alpha-aryl-alpha, beta-diamino acid ester is prepared through one-step reaction of a diazo compound, amide and imine as raw materials in an organic solvent under the catalysis of a metal catalyst. The synthesis method has the advantages of high atom economy, high selectivity, mild reaction conditions and simple and safe operation. The prepared derivative containing the alpha-aryl-alpha, beta-diamino acid ester can be used as an important chemical and medical intermediate, has biological activity and is suitable for preparation of drugs for resisting colon cancer and liver cancer.

Description

technical field [0001] The invention relates to the field of synthetic medicine and chemical industry, and mainly relates to an α-aryl-α, β-diamino acid ester derivative and its rapid and highly selective chemical synthesis method and application. Background technique [0002] α-quaternary carbon chiral central amino acid (C α -Tetrasubstitutedα-amino acids) is the central framework for constructing natural products and synthesizing some important drugs. It has biological activities such as antibacterial, antitumor, and anticancer. Hot topics in the field of chemistry. In recent years, TakeoKawabata has used the enol rearrangement of Clayden esters to obtain asymmetric α-aryl amino acid derivatives (J.Am.Chem.Soc.2013,135,13294-13297); Boris J.Nachtsheim found that alkynyl iodonium salts The α-quaternary carbon chiral center amino acid derivatives can be rapidly obtained by mediating the alkynylation reaction of Azlactones (Org. Lett. 2014, 16, 1326-1329). After that, new...

Claims

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Application Information

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IPC IPC(8): C07C233/49C07C233/47C07C231/08C07D333/24C07D307/54A61P35/00
CPCC07C231/08C07C233/47C07C233/49C07D307/54C07D333/24
Inventor 刘顺英雷锐锐贾凯莉吴永刘冬岚董素珍胡文浩
Owner EAST CHINA NORMAL UNIV
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