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Method for preparing gamma-carbonyl carboxylic acid, amino acid, amino acid ester and amide compounds

A carbonyl amino acid ester and carbonyl amino acid technology, which is applied in the field of preparation of γ-carbonyl carboxylic acid, amino acid ester and amide compounds, and amino acids, and can solve the problems of high price, limited application, difficult recovery and recycling of homogeneous catalysts, etc.

Active Publication Date: 2015-01-14
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the use of expensive homogeneous catalysts in the reaction, which is not easy to recover and recycle, its application in the synthesis industry is limited.

Method used

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  • Method for preparing gamma-carbonyl carboxylic acid, amino acid, amino acid ester and amide compounds
  • Method for preparing gamma-carbonyl carboxylic acid, amino acid, amino acid ester and amide compounds
  • Method for preparing gamma-carbonyl carboxylic acid, amino acid, amino acid ester and amide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1, the preparation of compound 1 (method one)

[0033] The reaction equation is as follows:

[0034]

[0035] Place 1 mmol of n-valeric acid (102 mg) in a 25 mL reaction vessel with a polytetrafluoroethylene stopcock, add 2 times the amount of oxidant potassium persulfate K 2 S 2 o 8 (2mmol, 540mg), dissolved in 5mL of distilled water and heated at 100°C for 4 hours. After the reaction, the reaction system was cooled to room temperature, extracted three times by adding ethyl acetate (10 mL×3 times), and the organic phase was washed with anhydrous Na 2 SO 4 After drying, it was spin-dried and purified by column chromatography (the volume ratio of dichloromethane:methanol was 15:1). The reaction was monitored by thin-layer chromatography, visualized with bromophenol blue or CAM.

[0036] The structural confirmation data of this product are as follows:

[0037] 1 H NMR (400MHz, CDCl 3 ): δ(ppm) 2.20(s, 3H), 2.26(t, J=6.4Hz, 2H), 2.76(t, J=6.4Hz, 2H)....

Embodiment 2

[0039] Embodiment 2, the preparation of compound 2 (method one)

[0040] The reaction equation is as follows:

[0041]

[0042] Put 1mmol of 2-methyl-n-valeric acid (116mg) in a 25mL reaction vessel with a polytetrafluoroethylene stopcock, add 2 times the amount of oxidant potassium persulfate K 2 S 2 o 8 (2mmol, 540mg), dissolved in 10mL of distilled water, and heated at 100°C for 6 hours. After the reaction, the reaction system was cooled to room temperature, extracted three times by adding ethyl acetate (10 mL×3 times), and the organic phase was washed with anhydrous Na 2 SO 4 After drying, it was spin-dried and purified by column chromatography (the volume ratio of dichloromethane:methanol was 15:1). The reaction was monitored by thin-layer chromatography, visualized with bromophenol blue or CAM.

[0043] The structural confirmation data of this product are as follows:

[0044] 1 H NMR (400MHz, CDCl 3 ): δ(ppm) 1.23(d, J=6.8Hz, 3H), 2.18(s, 3H), 2.44-2.55(m, 1H...

Embodiment 3

[0046] Embodiment 3, the preparation of compound 3 (method one)

[0047] The reaction equation is as follows:

[0048]

[0049] Put 1 mmol of 3-methyl-n-valeric acid (116 mg) in a 25 mL reaction vessel with a polytetrafluoroethylene stopcock, add 2 times the amount of oxidant potassium persulfate K 2 S 2 o 8 (2mmol, 540mg), dissolved in 10mL of distilled water, and heated at 100°C for 12 hours. After the reaction, the reaction system was cooled to room temperature, extracted three times by adding ethyl acetate (10 mL×3 times), and the organic phase was washed with anhydrous Na 2 SO 4After drying, it was spin-dried and purified by column chromatography (the volume ratio of dichloromethane:methanol was 15:1). The reaction was monitored by thin-layer chromatography, visualized with bromophenol blue or CAM.

[0050] The structural confirmation data of this product are as follows:

[0051] 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 1.18 (d, J = 7.2Hz, 3H), 2.23 (s, 3H), 2.31-2....

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Abstract

The invention discloses a method for preparing gamma-carbonyl carboxylic acid, amino acid, amino acid ester and amide compounds. The method comprises the following steps: uniformly mixing a methylene-containing compound, an oxidizing agent and water to perform selective methylene carbon-hydrogen bond oxidation, so as to obtain at least one of gamma-carbonyl carboxylic acid, gamma-carbonyl amino acid and gamma-carbonyl amide compounds after the reaction is finished. The method is a methylene selective oxidation reaction which does not need a catalyst for catalysis and employs a persulfate as an oxidizing agent, and the reaction is successfully applied to oxidation of methylene carbon-hydrogen bonds of carboxylic acids, amino acids and amide compounds, excellent selectivity is obtained, and the method has important application value.

Description

technical field [0001] The invention relates to a method for preparing gamma-carbonyl carboxylic acid, amino acid, amino acid ester and amides. Background technique [0002] Methylene is widely present in various organic compound molecules. Since methylene does not react with most chemical reagents and there are multiple chemically unequal methylene in an organic molecule, the selective oxidation of methylene has long been a challenge in synthetic chemistry. A major challenge. At present, methylene oxidation mainly relies on natural enzyme compounds such as cytochrome P450 (Nature.2004, 432, 829), bionic non-enzyme iron catalysts (Science. 566; Angew.Chem.Int.Ed.2009, 48, 5720; Angew.Chem.Int.Ed.2012, 51, 3448.), and complex metal cluster complex catalysts (Nat.Chem.2010, 2, 478) and oxidizing agents to achieve. However, due to the use of expensive homogeneous catalysts in the reaction, which is not easy to recover and recycle, its application in the synthesis industry i...

Claims

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Application Information

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IPC IPC(8): C07C51/373C07C59/185C07C59/84C07D209/48C07D213/81
CPCC07C51/373C07C59/185C07C59/84C07D209/48C07D213/81
Inventor 施章杰李鑫
Owner PEKING UNIV
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