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5,5,5-trifluoro-4-(3-methyl phenylimino) methyl valerate and its preparation method

A technology of methyl aniline and methyl valerate, applied in the field of organic compound synthesis technology, can solve the problems such as limitation of physiological activity of fluorine-containing amino acids, lack, lack of synthesis means, etc., and achieves high yield, easy operation, raw material easy-to-get effect

Inactive Publication Date: 2007-05-30
JIANGSU TIANCHENG BIOCHEM PROD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the widespread lack of such compounds in nature and the lack of effective synthesis methods, the research on the physiological activities of such fluorine-containing amino acids is largely limited.

Method used

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  • 5,5,5-trifluoro-4-(3-methyl phenylimino) methyl valerate and its preparation method
  • 5,5,5-trifluoro-4-(3-methyl phenylimino) methyl valerate and its preparation method
  • 5,5,5-trifluoro-4-(3-methyl phenylimino) methyl valerate and its preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0021] The processing steps in the present embodiment are as follows:

[0022] Under the protection of nitrogen, add 5,5,5-trifluoro-4-carbonyl-pentanoic acid methyl ester 10mmol, 1.9 g in a three-necked flask with a volume of 50 ml; 3-methylaniline 10 mmol, 1.1 g; solvent toluene 25 ml; and catalyst p-toluenesulfonic acid 1 mmol, 0.20 g. Then install a water separator and a reflux condenser, heat to reflux for 72 hours, and the heating temperature is 140°C; at the same time, stir continuously to make the reaction complete; after the reaction is completed, the solvent is evaporated under reduced pressure; the crude product is separated by silica gel column chromatography, and the silica gel column layer Ethyl acetate in the analysis: sherwood oil=1: 4; Finally, 2.0 grams of light yellow target compound 5,5,5-trifluoro-4-(3-methylphenylimino) methyl pentanoate was obtained. The rate is 73%.

Embodiment 2

[0024] The processing steps in the present embodiment are as follows:

[0025] Under nitrogen protection, in a three-necked flask with a volume of 100 ml, 10 mmol, 1.9 grams of 5,5,5-trifluoro-4-carbonyl-valeric acid methyl ester were added; 15 mmol, 1.6 grams of 3-methylaniline; the solvent toluene 50 ml; and catalyst p-toluenesulfonic acid 1 mmol, 0.20 g. Then install a water separator and a reflux condenser, heat and reflux for 80 hours, and the heating temperature is 140°C; at the same time, stir continuously to make the reaction complete; after the reaction is completed, the solvent is evaporated under reduced pressure; the crude product is separated by silica gel column chromatography, and the silica gel column layer Ethyl acetate in the analysis: sherwood oil=1: 4; Finally, 2.2 grams of light yellow target compound 5,5,5-trifluoro-4-(3-methylphenylimino) methyl pentanoate was obtained. The rate is 81%.

Embodiment 3

[0027] The processing steps in the present embodiment are as follows:

[0028] Under the protection of nitrogen, add 5,5,5-trifluoro-4-carbonyl-pentanoic acid methyl ester 10mmol, 1.9 g in a three-necked flask with a volume of 250 ml; 3-methylaniline 3 mmol, 3.2 g; solvent toluene 100 ml; and catalyst p-toluenesulfonic acid 1 mmol, 0.20 g. Then install a water separator and a reflux condenser, heat and reflux for 100 hours, and the heating temperature is 140°C; at the same time, stir continuously to make the reaction complete; after the reaction is completed, the solvent is evaporated under reduced pressure; the crude product is separated by silica gel column chromatography, and the silica gel column layer Ethyl acetate in the analysis: sherwood oil=1: 4; Finally, 2.2 grams of light yellow target compound 5,5,5-trifluoro-4-(3-methylphenylimino) methyl pentanoate was obtained. The rate is 81%.

[0029] The product obtained in the above examples was detected by infrared spectr...

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Abstract

The invention discloses a 5, 5, 5-trifluoro-4-(3-methyl benzaimino) valerianic methyl ester and making method, which comprises the following steps: adopting benzene or toluene as solvent; adding 5, 5, 5-trifluoro-4-carbonyl valerianic methyl ester and 3-methyl phenylamine in the reacting container protected by nitrogen as well as benzene or toluene; heating to 48-72h acted by catalyst; heating to 100-120 deg.c or 130-150 deg.c; stirring continuously; decompressing; evaporating solvent; separating crude product through silica gel column layer technique; obtaining light yellow compound.

Description

technical field [0001] The invention relates to a novel fluorine-containing intermediate 5,5,5-trifluoro-4-(3-methylphenylimino)methyl valerate and a preparation method thereof, belonging to the technical field of organic compound synthesis technology. Background technique [0002] Fluorine-containing organic compounds have gradually penetrated into every aspect of our life, so fluorine-containing compounds have become the new favorite of organic chemists. The 21st century is hailed as the century of electronics and bioengineering, so amino acids, which are the basic constituent units of proteins in human life, have entered an unprecedented era of research, and the research on fluorine-containing amino acids is even more refreshing. Fluorine-containing amino acids, especially fluorine-containing β- or γ-amino acids have special physiological activities, and have extremely high research value in drug synthesis and treatment of various human diseases. [0003] Due to the wide...

Claims

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Application Information

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IPC IPC(8): C07C251/08C07C249/02
Inventor 万文麻国斌陈华袁宗谦郝健
Owner JIANGSU TIANCHENG BIOCHEM PROD
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