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Carboxylic acid betaine type fluorine-containing compound as well as synthesis method and application thereof

A technology of carboxybetaine and synthesis method, which is applied in the directions of cyanide reaction preparation, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as difficult quantitative detection and quantitative research, and achieve high yield, Easy separation, simple purification method

Active Publication Date: 2019-06-25
INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Third, no radioactivity
for 1 H MRI contrast agent can provide physiological and pathological information of the body by changing the relaxation rate of water protons in local tissues and enhancing the contrast between normal and lesion sites, but it is difficult to achieve quantitative detection and quantitative research

Method used

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  • Carboxylic acid betaine type fluorine-containing compound as well as synthesis method and application thereof
  • Carboxylic acid betaine type fluorine-containing compound as well as synthesis method and application thereof
  • Carboxylic acid betaine type fluorine-containing compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The synthesis of embodiment 1 compound C1

[0025] See the applicant's application on the same day, titled "Fluorinated tertiary amine compound and its synthesis method and its application" to obtain the starting tertiary amine compound, wherein, the method for newly synthesizing the fluorinated secondary amine compound is detailed in the applicant's application on the same day , named: fluorinated secondary amine compound and its synthesis method and application.

[0026] The chemical structure of compound C1 is shown in the following formula. The specific synthesis steps are as follows: First, 2-((2-fluoroethyl)methylamino)ethyl methacrylate (10 mmol), tert-butyl bromoacetate (1.5 eq.) were dissolved in anhydrous acetonitrile, and Under air protection, at 50 o C in a constant temperature oil bath for 24 h. After the reaction, the solvent was distilled off under reduced pressure and separated by column chromatography, using the DCM (dichloromethane) / methanol mixture...

Embodiment 2

[0029] Example 2 Synthesis of Compound C2

[0030] The chemical structure of compound C2 is shown in the following formula. The specific synthesis steps are as follows: First, 2-((2,2-difluoroethyl)methylamino)ethyl methacrylate (10 mmol), tert-butyl bromoacetate (1.5 eq.) were dissolved in anhydrous acetonitrile , under argon protection, at 50 o C in a constant temperature oil bath for 24 h. After the reaction, the solvent was distilled off under reduced pressure and separated by column chromatography. The eluent containing the target compound was collected with the DCM / methanol mixture as the eluent. After removing the solvent, the quaternary ammonium salt protected by tert-butyl group was obtained. product. Further, the tert-butyl protected quaternary ammonium salt product (1.0 eq.), triethylsilane (2.5 eq.) was dissolved in anhydrous DCM, and trifluoroacetic acid (13 eq.) was added dropwise under ice bath conditions, After returning to room temperature, the reaction wa...

Embodiment 3

[0033] Synthesis of Example 3 Compound C3

[0034] The chemical structure of compound C3 is shown in the following formula. The specific synthesis steps are as follows: First, 2-((3,3,3-trifluoropropyl)methylamino)ethyl methacrylate (10 mmol), tert-butyl bromoacetate (1.5 eq.) were dissolved in anhydrous In acetonitrile, under the protection of argon, at 50 o C in a constant temperature oil bath for 24 h. After the reaction, the solvent was distilled off under reduced pressure and separated by column chromatography. The eluent containing the target compound was collected with the DCM / methanol mixture as the eluent. After removing the solvent, the quaternary ammonium salt protected by tert-butyl group was obtained. product. Further, the tert-butyl protected quaternary ammonium salt product (1.0 eq.), triethylsilane (2.5 eq.) was dissolved in anhydrous DCM, and trifluoroacetic acid (13 eq.) was added dropwise under ice bath conditions, After returning to room temperature, th...

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Abstract

The invention relates to a carboxylic acid betaine type fluorine-containing compound as well as a synthesis method and application thereof. A fluorinated tertiary amine compound as an initial raw material is reacted with tert-butyl bromoacetate to obtain a tert-butyl-protected quaternary ammonium salt product; the tert-butyl-protected quaternary ammonium salt product and triethyl silane are dissolved in anhydrous DCM, trifluoroacetic acid is dropwise added under an ice bath condition, the reaction is continued after the mixture is recovered to the room temperature, reduced pressure distillation is performed to remove a solvent and the trifluoroacetic acid, a product is dissolved by using a hydrochloric acid solution, and then is subjected to freeze-drying, the residual trifluoroacetic acidis removed by replacement, and the carboxylic acid betaine type fluorine-containing compound is finally obtained. The preparation method disclosed by the invention can be used for preparing a fluorinated polymer, the preparation method is simple, the yield is high, the separation is easy, and the purity is high. The compound contains a plurality of chemical active groups such as hydroxyl, amino,carboxyl, acetenyl, azido, and sulfydryl, can be used for labeling a drug, a polymer, a nanocarrier and an implant material, and satisfies the requirements of 19F MRI probe development.

Description

technical field [0001] The invention relates to a carboxybetaine type fluorine-containing compound and its synthesis method and application. Background technique [0002] In order to adapt to the improvement and rapid development of modern medical imaging requirements, the study of new MRI probes has become a research hotspot. in 19 F has great potential as a quantitative MRI contrast agent. First, there is no endogenous background interference. compared to 1 HMRI is trapped by the strong background interference caused by the ubiquitous water molecules in the body, and only a small amount (<10 -6 M) Fluorine exists in bones and teeth in the form of solid fluorine compounds ( T 2 →0 ),Far below 19 The detection limit of F MRI avoids continuous sampling and comparison of images before and after contrast agents, which is necessary in other molecular imaging using superparamagnetic (such as iron oxide) and paramagnetic metals (such as gadolinium). Therefore, the acc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/12C07C227/18C08G63/91C08G69/48
Inventor 黄平升王伟伟宋会娟孔德领
Owner INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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