A kind of synthetic method of n-nitroso-4-aminobutyrate compound

A technology of aminobutyrate and synthesis method, which is applied in the field of synthesis of ester compounds, and can solve problems such as harsh reaction conditions, practical limitations, and difficult availability of reaction raw materials

Active Publication Date: 2021-08-20
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these methods can effectively synthesize N-nitroso-4-aminobutyrate compounds, there are still some problems that need to be solved urgently, such as: the reaction raw materials are not easy to obtain, the reaction conditions are harsh, and the synthesis steps are cumbersome. However, the practicability of the above method is greatly limited

Method used

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  • A kind of synthetic method of n-nitroso-4-aminobutyrate compound
  • A kind of synthetic method of n-nitroso-4-aminobutyrate compound
  • A kind of synthetic method of n-nitroso-4-aminobutyrate compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013]

[0014] Add compound 1a (0.2mmol, 32mg) and ethanol (C 2 h 5 OH, 1mL), then add 2,2,6,6-tetramethyl-1-piperidine tetrafluoroborate (T + BF 4 - , 0.3mmol, 73mg) and TBN (90wt%, 0.6mmol, 79μL). The reaction was stirred at room temperature under an air atmosphere for 6 hours, then 10 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=20:1, v / v) to obtain yellow liquid product N-nitroso-N-phenyl-4-aminobutyric acid ethyl ester 2a (30mg ,64%). The characterization data of this compound are as follows: 1 H NMR (600MHz, CDCl 3 )δ:1.17-1.20(m,3H),1.80-1.83(m,2H),2.25(t,J=7.2Hz,2H),4.01-4.08(m,4H),7.28-7.31(m,1H) ,7.40-7.43(m,2H),7.51-7.53(m,2H). 13 C NMR (100MHz, CDCl 3 )δ: 14.2, 21.7, 31.3, 42.8, 60.7, 119.3, 127.4, 129.6, 141.5, 172.6. MS: m / z...

Embodiment 2

[0016] Add compound 1a (0.2mmol, 32mg) and ethanol (C 2 h 5 OH, 1mL), then add 2,2,6,6-tetramethyl-1-piperidine tetrafluoroborate (T + BF 4 - , 0.4mmol, 97mg) and TBN (90wt%, 0.6mmol, 79μL). The reaction was stirred at room temperature under an air atmosphere for 6 hours, then 10 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20:1, v / v) to obtain yellow liquid product 2a (25 mg, 53%).

Embodiment 3

[0018] Add compound 1a (0.2mmol, 32mg) and ethanol (C 2 h 5 OH, 1mL), then add 2,2,6,6-tetramethyl-1-piperidine perchlorate (T + ClO 4 - , 0.3mmol, 77mg) and TBN (90wt%, 0.6mmol, 79μL). The reaction was stirred at room temperature under an air atmosphere for 6 hours, then 10 mL of saturated sodium chloride solution was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20:1, v / v) to obtain yellow liquid product 2a (20 mg, 42%).

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Abstract

The invention discloses a method for synthesizing N-nitroso-4-aminobutyrate compounds, which belongs to the technical field of synthesis of ester compounds. The main points of the technical scheme of the present invention are: compared with the prior art, the present invention has the following advantages: (1) the synthesis process is a one-pot series reaction, which is easy to operate and high in efficiency; (2) the raw materials are easy to obtain; (3) the reaction takes place in 60 It can be carried out below ℃, the conditions are mild, and the operation is simple; (4) the scope of application of the substrate is wide.

Description

technical field [0001] The invention belongs to the technical field of synthesis of ester compounds, and in particular relates to a synthesis method of N-nitroso-4-aminobutyrate compounds. Background technique [0002] N-nitroso-4-aminobutyrate compounds contain highly reactive nitroso and ester functional groups at the same time. As important organic synthesis intermediates, they have a wide range of applications in the fields of biopharmaceuticals, pesticides and industrial dyes. Applications. At present, the synthesis methods of such compounds mainly include: 1) nucleophilic substitution-nitrosation reaction of primary amine and bromobutyrate; 2) Michael addition-decarboxylation-nitrosation reaction of substituted glycine and acrylate; 3) Double nucleophilic substitution-nitrosation reactions of primary amines with 4-chlorobutyryl chloride and alcohols, etc. Although these methods can effectively synthesize N-nitroso-4-aminobutyrate compounds, there are still some probl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C243/06C07C241/00C07C253/30C07C255/65
Inventor 何艳宋桂娴范学森刘奇梦柴欣媛孙楠
Owner HENAN NORMAL UNIV
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