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Method for synthesizing alpha-amino acid

A synthesis method and amino acid technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as harsh conditions, achieve cheap and easy-to-obtain raw materials, and avoid the effect of subsequent purification operations

Active Publication Date: 2018-10-19
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that only acrylamine raw materials can be used, and the conditions are very harsh, and strong alkali and high-pressure carbon dioxide must be used

Method used

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  • Method for synthesizing alpha-amino acid
  • Method for synthesizing alpha-amino acid
  • Method for synthesizing alpha-amino acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] 2-(Benzylamino)-2,2-diphenylacetic acid dicyclohexylamine salt (4a).

[0064]

[0065] According to the typical experimental procedure, with ketimine N-benzyl-1,1-diphenylmethanimine (54.2 mg, 0.2 mmol), catalyst iridium-7 (0.9 mg, 0.5mol%), N, N- Dicyclohexylmethylamine (85.6 μL, 0.4 mmol), carbon dioxide (in balloon), 2 mL of acetonitrile, and the reaction was performed. After the reaction, the target product was obtained by filtration, which was a white solid with a melting point of 154.9-155.5°C (90.8 mg, yield 91%).

[0066] 1H NMR (400MHz, CDCl3): δ7.60(d, J=7.2Hz, 4H), 7.31(d, J=7.0Hz, 2H), 7.28-7.22(m, 6H), 7.21-7.14(m, 3H ), 3.31 (s, 2H), 2.66 (t, J=10.8Hz, 2H, Cy), 1.85-1.43 (m, 10H, Cy), 1.34-0.81 (m, 10H, Cy) ppm;

[0067] 13C{1H}NMR (100MHz, CDCl3): δ177.06, 144.50, 141.82, 129.44, 128.47, 128.20, 127.23, 126.57, 126.11, 74.16, 52.25(Cy), 48.80, 28.95(Cy), 25.17(Cy), 24.87 (Cy) ppm;

[0068] IR (thin film): 2928, 2853, 1632, 1360, 1347, 1117, 1098, 7...

Embodiment 2

[0071] 2-((2-chlorobenzyl)amino)-2,2-diphenylacetic acid dicyclohexylamine salt (4b)

[0072]

[0073] According to the typical experimental procedure, with ketimine N-(2-chlorobenzyl)-1,1-diphenylmethanimine (61.2 mg, 0.2 mmol), catalyst iridium-7 (0.9 mg, 0.5mol%) , N,N-Dicyclohexylmethylamine (85.6 μL, 0.4 mmol), carbon dioxide (in balloon), 2 mL of acetonitrile, and the reaction was carried out. After the reaction, the target product was obtained by filtration, which was a white solid with a melting point of 138.5-139.6°C (94.9 mg, yield 89%).

[0074] 1H NMR (400MHz, CDCl3): δ7.62(d, J=7.2Hz, 4H), 7.53(dd, J=7.6, 1.7Hz, 1H), 7.30-7.22(m, 5H), 7.22-7.09(m , 4H), 3.40 (s, 2H), 2.67 (t, J=10.9Hz, 2H, Cy), 1.81-1.28 (m, 10H, Cy), 1.20-0.70 (m, 10H, Cy) ppm;

[0075] 13C{1H}NMR (100MHz, CDCl3): δ176.85, 144.24, 139.34, 133.57, 129.96, 129.23, 128.97, 127.54, 127.08, 126.58, 125.96, 73.90, 52.09(cy), 45.89, 28.61( (cy), 24.71 (cy) ppm.ppm;

[0076] IR (thin film): 2940, ...

Embodiment 3

[0079] 2-((3-chlorobenzyl)amino)-2,2-diphenylacetic acid dicyclohexylamine salt (4c)

[0080]

[0081] According to the typical experimental procedure, with ketimine N-(3-chlorobenzyl)-1,1-diphenylmethanimine (61.2 mg, 0.2 mmol), catalyst iridium-7 (0.9 mg, 0.5mol%) , N,N-Dicyclohexylmethylamine (85.6 μL, 0.4 mmol), carbon dioxide (in balloon), 2 mL of acetonitrile, and the reaction was carried out. After the reaction, the target product was obtained by filtration, which was a white solid with a melting point of 148.0-149.6°C (96 mg, yield 90%).

[0082] 1H NMR (400MHz, CDCl3): δ7.58(d, J=7.4Hz, 4H), 7.36-7.11(m, 10H), 3.27(s, 2H), 2.66(brs, 2H, Cy), 1.84-1.45 (m, 10H, Cy), 1.16-0.93 (m, 10H, Cy) ppm;

[0083] 13C{1H}NMR (100MHz, CDCl3): δ176.95, 144.33, 144.05, 133.98, 129.41(x2), 128.42, 127.28, 126.67, 126.59, 126.21, 74.08, 52.28(Cy), 48.39, 28.90(Cy), 25.17(Cy), 24.85(Cy)ppm;

[0084] IR (thin film): 2935, 1627, 1551, 1447, 1358, 1349, 810, 705cm-1;

[0085] HRMS ...

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Abstract

The invention discloses a method for synthesizing an alpha-amino acid, and belongs to the fields of organic chemistry, medicinal chemistry and protein chemistry. The method uses sunlight or visible light as an energy source, is added with an electron donor, and uses carbon dioxide and an imine compound as raw materials for synthesizing the alpha-amino acid at normal temperature and normal pressure. The method adopts cheap and readily available raw materials, uses extremely mild reaction conditions, avoids expensive and dangerous high-pressure reaction devices by using a carbon dioxide gas at the normal pressure, can use clean and infinite sunlight as the energy source, and eliminates subsequent purification operations by automatically separating out products from a system in a solid form after completing the reaction and simply filtering to obtain a target product.

Description

technical field [0001] The invention relates to the fields of organic chemistry, medicinal chemistry and protein chemistry, in particular to a method for preparing α-amino acid by means of organic synthesis. Background technique [0002] α-amino acid is the basic skeleton of protein, and it plays a very important role in many fields such as protein synthesis, organic chemistry, and medicinal chemistry. And the method for chemically synthesizing α-amino acid commonly used at present mostly has various shortcomings, for example the method for cyanide needs to use highly toxic raw material, and the raw material used by other methods is expensive. [0003] Synthesis of α-amino acids using carbon dioxide as a raw material will be a very promising method. However, the existing methods of using carbon dioxide all need to use harsh reaction conditions, such as high-pressure gas, high-temperature reaction, etc., which make large-scale production difficult and cause a large amount of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/36C07C227/12C07D213/38C07D333/20C07D307/52C07D333/24
CPCC07C229/36C07D213/38C07D307/52C07D333/20C07D333/24
Inventor 樊新元龚旭马梦月汪锐
Owner NANJING UNIV OF TECH
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