Synthesis method of (+/-)-alpha-fluoro-gamma-amino acid

A synthesis method and amino acid technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as low yield, and achieve the effects of high yield, simple product separation and short process flow

Active Publication Date: 2018-02-09
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, this method also uses the highly toxic and flammable fluorine reagent DAST, and the yield is low

Method used

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  • Synthesis method of (+/-)-alpha-fluoro-gamma-amino acid
  • Synthesis method of (+/-)-alpha-fluoro-gamma-amino acid
  • Synthesis method of (+/-)-alpha-fluoro-gamma-amino acid

Examples

Experimental program
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Embodiment 1

[0032]

[0033] Reaction: 3-Phenyl-1-propanamine (2.0 g, 14.8 mmol) and phthalic anhydride (2.192 g, 14.8 mmol) were dissolved in 20 mL of dry chloroform. Reflux at 80°C for 4h. Then it was quenched with 10 mL of water, extracted three times with ethyl acetate, and the organic phase was collected and dried over anhydrous magnesium sulfate. Separation with a chromatographic column (petroleum ether: ethyl acetate = 14:1) yielded 2.745 g of the product with a yield of 70%. The characterization data are as follows:

[0034] 2-(3-phenylpropyl)isoindoline-1,3-dione; 1 H NMR (400MHz, CDCl 3 )δ (ppm) 7.80 (dd, J = 3.13, 5.5Hz, 2H), 7.67 (dd, J = 2.95, 5.38Hz, 2H), 7.27-7.09 (m, 5H), 3.73 (t, J = 7.17Hz ,2H),2.67(t,J=7.51Hz,2H),2.02(tt,J=6.54,7.42Hz,2H); 13 C NMR (100MHz, CDCl 3 ): δ168.3, 141.0, 133.8, 132.1, 128.4, 128.3, 125.9, 123.1, 37.8, 33.2, 29.9;

[0035]

[0036] Reaction: Take a 100mL round bottom flask, add imide (1.19g, 4.5mmol), selectfluor (1.594g, 4.5mmol) ...

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Abstract

The invention discloses a synthesis method of (+ / -)-alpha-fluoro-gamma-amino acid. The method comprises the steps of enabling 3-phenyl-1-propylamine or 3-phenyl-1-propylamine derivatives to be sequentially subjected to four reaction, i.e., amido protection, benzyl free radical fluorination, benzene ring oxidation and protecting group removal. The method avoids the use of a high-risk fluorine reagent DAST, and has the characteristics of being simple to operate, rapid in reaction, high in yield and the like.

Description

technical field [0001] The present invention relates to a synthetic method of fluorinated amino acid, in particular to a method of using 3-phenyl-1-propanamine derivatives as raw material, which undergoes sequentially protective amino reaction, free radical fluorination reaction, benzene epoxidation reaction and deprotection group The invention relates to a method for efficiently and rapidly synthesizing (±)-α-fluoro-γ-amino acid, which belongs to the technical field of synthesis of polypeptide synthons and pharmaceutical intermediates. Background technique [0002] As early as 1965, Buchanan, R.L.; Pattison, F.L.M et al. reported a method for synthesizing α-fluoro-γ-amino acids in the Canadian Journal of Chemistry. The key step of the method is to use the nucleophilic addition reaction between the ternary nitrogen heterocyclic intermediate and diethyl 2-fluoromalonate, and then hydrolyze the amide bond and ester group under concentrated acid to obtain the target product. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48C07C227/18C07C229/20
Inventor 胡祥国刘清泉陈宏伟喻熙
Owner JIANGXI NORMAL UNIV
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