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

Synthesis method of glycine derivatives

A technology of glycine derivatives, which is applied in the field of preparation of glycine derivatives, can solve the problems of heavy metal pollution, inability to use large-scale production, expensive catalysts, etc., achieve fast reaction speed, wide application range of substrates, and easy access to catalysts Effect

Inactive Publication Date: 2015-08-12
TONGJI UNIV
View PDF3 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003]The many methods in the past mainly include Strecker, Ugi and Petais reactions ((a) Strecker, A. Ann. Chem. Pharm. 1850, 75, 27–45; (b) Ugi, I. Angew. Chem., Int. Ed. Engl. 1962, 1, 8–20; (c) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445–446.) and the use of photocatalysts to absorb energy to stimulate chemical reactions and the construction of carbon-carbon bonds in organic matter has attracted more and more attention. The most famous method for preparing similar compounds using visible light is Magnus Rueping (Zhu, S. Q.; Rueping, M. Chem. Commun.2012, 48, 11960-11962.) The catalyst used is Ir(ppy)2(bpy)PF6 Although this method can also successfully achieve the goal, it cannot be used in large-scale production due to the high cost of the catalyst, just like ruthenium-based catalysts. problems such as heavy metal pollution

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
  • Synthesis method of glycine derivatives
  • Synthesis method of glycine derivatives
  • Synthesis method of glycine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0036] Reaction equation:

[0037]

[0038] where the Lewis acid is FeCl 2 , the solvent is acetonitrile, the catalyst EosinY,

[0039] Proceed as follows:

[0040] In a dry reaction tube, sequentially add 0.1mmol of glycine ester compound, 0.12mmol of indole, 0.005mmol of EosinY, FeCl 2 0.01 mmol.

[0041] Introduce oxygen at an atmospheric pressure, and irradiate with a blue LED for 40 hours. After the reaction, pass through a diatomaceous earth sand core, and remove the solvent under reduced pressure. The product is subjected to column chromatography to obtain the target product (petroleum ether / ethyl acetate = 40 / 1).

[0042] Yield 93%;

[0043]

[0044] 1 H NMR (400 MHz, CDCl 3) δ 8.19 (s, 1H), 7.82 (d, J = 7.8 Hz, 1H), 7.31 (d, J = 8.0 Hz, 1H), 7.20 (dd, J = 15.9, 8.5 Hz, 2H), 7.15 (s, 1H), 6.96 (d, J = 8.1 Hz, 2H), 6.56 (d, J = 8.2 Hz, 2H), 5.36 (s, 1H), 4.62 (s, 1H), 4.23 – 4.08 (m, 2H), 2.21 (s, 3H), 1.20 (t, J = 7.1 Hz, 3H). 13 C NMR (101 M...

Embodiment 3

[0047] Reaction equation:

[0048]

[0049] where the Lewis acid is FeCl 2 , the solvent is acetonitrile, the catalyst EosinY,

[0050] Proceed as follows:

[0051] In a dry reaction tube, sequentially add 0.1mmol of glycine ester compound, 0.12mmol of indole, 0.005mmol of EosinY, FeCl 2 0.01 mmol.

[0052] Introduce oxygen at an atmospheric pressure, and irradiate with a blue LED for 40 hours. After the reaction, pass through a diatomaceous earth sand core, and remove the solvent under reduced pressure. The product is subjected to column chromatography to obtain the target product (petroleum ether / ethyl acetate = 40 / 1).

[0053] Yield 89%;

[0054]

[0055] 1 H NMR (400 MHz, CDCl 3 ) δ 8.22 (s, 1H), 7.80 (d, J = 7.8 Hz, 1H), 7.33 (d, J = 8.0 Hz, 1H), 7.24 – 7.20 (m, 1H), 7.20 – 7.15 (m, 1H), 7.14 (s, 1H), 7.06 (d, J = 8.7 Hz, 2H), 6.52 (d, J = 8.8 Hz, 2H), 5.33 (s, 1H), 4.79 (s, 1H), 4.26 – 4.08 (m, 2H), 1.20 (t, J = 7.1 Hz, 3H). 13 C NMR (101 MHz, CD...

Embodiment 4

[0058] Reaction equation:

[0059]

[0060] where the Lewis acid is FeCl 2 , the solvent is acetonitrile, the catalyst EosinY,

[0061] Proceed as follows:

[0062] In a dry reaction tube, add glycine ester compound 0.1mmol, 5-nitroindole 0.12mmol, EosinY 0.005mmol, FeCl 2 0.01 mmol.

[0063] Introduce oxygen at an atmospheric pressure, and irradiate with a blue LED for 40 hours. After the reaction, pass through a diatomaceous earth sand core, and remove the solvent under reduced pressure. The product is subjected to column chromatography to obtain the target product (petroleum ether / ethyl acetate = 40 / 1).

[0064] Yield 90%;

[0065]

[0066] 1 H NMR (400 MHz, CDCl 3 ) δ 8.85 (s, 1H), 8.81 (s, 1H), 8.12 (d, J = 8.7 Hz, 1H), 7.42 – 7.32 (m, 2H), 7.15 (t, J = 7.4 Hz, 2H), 6.75 (t, J = 7.0 Hz, 1H), 6.63 (d, J = 7.7 Hz, 2H), 5.42 (s, 1H), 4.91 (s, 1H), 4.31 – 4.13 (m, 2H), 1.24 (t, J = 7.0 Hz, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 172.02 (s), 146.14 (s), 141...

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

No PUM Login to View More

Abstract

The invention relates to a synthesis method of glycine derivatives. The synthesis method comprises that in an organic solvent, a glycinate compound and indole as raw materials and a Lewis acid additive undergo a reaction in the presence of dye EosinY as a catalyst at a normal temperature in O2 atmosphere under pressure of 1 atm for 40h, and the products are separated and purified. Compared with the prior art, the synthesis method solves problems of low reaction efficiency, high temperature requirements, high catalyst cost and heavy metal pollution, has the characteristics of high reaction yield, simple operation and environmental friendliness, and can be widely used in organic synthesis methodology and natural product synthesis.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a preparation method of glycine derivatives, which especially has the characteristics of high reaction yield, simple and convenient operation, and environmental protection. Background technique [0002] Glycine derivatives are a class of compounds with high biological activity. As an important fragment of many organic compounds, it is widely used in organic chemistry, medicine, pesticide, chemical industry and other fields. [0003] Many methods in the past mainly include Strecker, Ugi and Petais reactions ((a) Strecker, A. Ann. Chem. Pharm . 1850, 75, 27–45; (b) Ugi, I. Angew. Chem., Int. Ed. Engl . 1962, 1, 8–20; (c) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc . 1997, 119, 445–446.) and the use of photocatalysts to absorb energy for stimulating chemical reactions and the construction of carbon-carbon bonds in organic matter has attracted more and more...

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
IPC IPC(8): C07D209/20C07D209/24
CPCC07D209/20C07D209/24
Inventor 陈余戈伟张荣华
Owner TONGJI UNIV
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