Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing amino acid derivative by utilizing photocatalysis micro-channel

A technology of derivatives and amino acids, applied in the field of chemical synthesis, can solve the problems of unfriendly environment, many synthesis steps, and limited application, and achieve the effects of shortened reaction time, simple operation, and high safety

Active Publication Date: 2020-05-22
NANJING UNIV OF TECH
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional preparation of amino acid derivatives often has many shortcomings such as many synthetic steps, serious energy waste, and unfriendly to the environment. These shortcomings limit its application in industrialization. The preparation method of the derivative is very meaningful

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing amino acid derivative by utilizing photocatalysis micro-channel
  • Method for preparing amino acid derivative by utilizing photocatalysis micro-channel
  • Method for preparing amino acid derivative by utilizing photocatalysis micro-channel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]

[0051] Weigh 0.0885g (0.5mmol, 1.0equiv) of N-acetyl-L-cysteine ​​methyl ester, 0.190g (1.0mmol, 2.0equiv) of ethyl 2-diazo-2-phenylacetate, and use 2.5mL di The methyl chloride is dissolved and loaded into the syringe after complete dissolution. The reaction solution is pumped into a reactor with a coil inner diameter of 0.5mm, the volume is 1mL, the flow rate of the microreactor is 0.1mL / min, irradiated with a blue LED light source (50W, 455nm), and the reaction is carried out at 25°C. The residence time 10min. After the reaction, TLC detection was performed, and 156.0 mg of the final product was obtained by column chromatography (petroleum ether: ethyl acetate = 1:1), with a yield of 92%. Such as image 3 , Figure 4 As shown, the characterization data are as follows: 1 H NMR (400MHz, Chloroform-d) δ7.48–7.39(m,2H),7.38–7.28(m,3H),6.37(d,J=33.7Hz,1H),4.86–4.76(m,1H), 4.67–4.55(m,1H),4.25–4.12(m,2H),3.74(d,J=16.6Hz,3H),2.96(s,2H),2.01(d,J=23.1Hz,3H),1.28 –1...

Embodiment 2

[0053] Weigh 0.0885g (0.5mmol, 1.0equiv) of N-acetyl-L-cysteine ​​methyl ester, 0.190g (1.0mmol, 2.0equiv) of ethyl 2-diazo-2-phenylacetate, and use 2.5mL di The methyl chloride is dissolved and loaded into the syringe after complete dissolution. The reaction solution is pumped into a reactor with a coil inner diameter of 0.5mm, the volume is 1mL, the flow rate of the microreactor is 0.1mL / min, irradiated with a blue LED light source (10W, 455nm), the reaction is carried out at 25°C, and the residence time 10min. After the reaction was completed, TLC detection was performed, and 128.9 mg of the product was obtained by column chromatography (petroleum ether: ethyl acetate = 1:1), with a yield of 76%.

Embodiment 3

[0055] Weigh 0.0885g (0.5mmol, 1.0equiv) of N-acetyl-L-cysteine ​​methyl ester, 0.190g (1.0mmol, 2.0equiv) of ethyl 2-diazo-2-phenylacetate, and use 2.5mL di The methyl chloride is dissolved and loaded into the syringe after complete dissolution. The reaction solution is pumped into a reactor with a coil inner diameter of 0.5mm, the volume is 1mL, the flow rate of the microreactor is 0.1mL / min, irradiated with a blue LED light source (50W, 455nm), and the reaction is carried out at 15°C. The residence time 10min. After the reaction was completed, TLC detection was performed, and 140.8 mg of the product was obtained by column chromatography (petroleum ether: ethyl acetate = 1:1), with a yield of 83%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
lengthaaaaaaaaaa
volumeaaaaaaaaaa
volumeaaaaaaaaaa
Login to View More

Abstract

The invention discloses a method for preparing an amino acid derivative by using a photocatalysis micro-channel. The method comprises the following steps: (1) dissolving a cysteine derivative and a diazonium acid ester compound in a solvent to prepare a homogeneous solution; (2) pumping the homogeneous solution prepared in the step (1) into a micro-reactor in a micro-channel reaction device provided with a light source for a reaction; and (3) collecting effluent of the microreactor to obtain the amino acid derivative. The reaction involved in the invention is a novel method for synthesizing the amino acid derivative, and the method does not need a homogeneous system added with a catalyst and other additives, and has good applicability to ortho-substituted diazonium acid ester, meta-substituted diazonium acid ester and para-substituted diazonium acid ester.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing amino acid derivatives by using photocatalytic microchannels. Background technique [0002] Amino acid is an essential substance for life, the basic unit of protein, and a good ligand. It has a multi-dentate coordination structure (N and O), and can coordinate with a variety of metal ions to form stable complexes. especially for transition metal ions. Furthermore, amino acids contain free amino groups (-NH 2 ) and carboxyl (-COOH), can combine with many hydrogen bond donors and acceptors through intermolecular hydrogen bonds to form a larger molecular structure. [0003] Visible light catalysis has attracted more and more attention in recent years. Compared with other catalytic methods, visible light catalysis can be carried out under milder conditions, and visible light as a sustainable energy source is more in line with environmental protec...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C323/59B01J19/12B01J19/00
CPCC07C319/14B01J19/0093B01J19/127C07C323/59
Inventor 郭凯覃龙州袁鑫邱江凯崔玉声孙蕲段秀庄恺强陈琳
Owner NANJING UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com