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Method for synthesizing alpha-amine formyl fluoroacetate compound

A technology for carbamoyl fluoroacetate and compounds, which is applied in the field of synthesizing α-carbamoyl fluoroacetate compounds, can solve the problems of cumbersome operation, low yield, and long reaction time, and achieve simple preparation and operation simple effect

Inactive Publication Date: 2015-04-08
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no systematic synthesis research on such compounds in the literature, and the conventional synthesis method of amides (Amino Acids & Biotic Resources. 2010, 32(1): 34-38) is not only cumbersome to operate, but also takes a long time to react, and produces rate is not high

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  • Method for synthesizing alpha-amine formyl fluoroacetate compound
  • Method for synthesizing alpha-amine formyl fluoroacetate compound
  • Method for synthesizing alpha-amine formyl fluoroacetate compound

Examples

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Effect test

Embodiment 1

[0017] In the reactor, 59 mg (1 mmol) of n-propylamine and 1.50 g (10 mmol) of dimethyl fluoromalonate were added, and the reaction was stirred at room temperature. The reaction was monitored by thin-layer chromatography. After 16 hours, the monitoring result showed that n-propylamine had reacted, and the reaction mixture was directly separated by column chromatography to obtain 188 mg of α-(N-propyl)carbamoyl fluoroacetate. The yield was 99%. The product was confirmed by NMR analysis, 1 H NMR (CDCl 3 ,500MHz,δ / ppm):6.43(br,1H),5.22(d,J=49.5Hz,1H),3.71(s,3H),3.32-3.23(m,2H),1.59-1.52(m,2H ), 1.31(t,J=7.3Hz,3H).

Embodiment 2

[0019] Into the reactor, 59 mg (1 mmol) of isopropylamine and 178 mg (1 mmol) of diethyl fluoromalonate were added, and stirred at room temperature for 8 hours. The mixture was directly separated by column chromatography to obtain 78 mg of ethyl α-(N-isopropyl)carbamoyl fluoroacetate in a yield of 41%. The product was confirmed by NMR analysis, 1 H NMR (CDCl 3 ,500MHz,δ / ppm):6.19(br,1H),5.19(d,J=49.0Hz,1H),4.36-4.26(m,2H),4.16-4.06(m,1H),1.32(t,J =7.3Hz, 3H), 1.19(t, J=6.0Hz, 6H).

Embodiment 3

[0021] Into the reactor, 194 mg (2 mmol) of 2-furylmethylamine and 1.78 g (10 mmol) of diethyl fluoromalonate were added, and stirred at room temperature for 16 hours. The reaction mixture was dispersed in 15 mL of ether, filtered, and the filter cake was washed with 5 mL of ether. The filter cake was recrystallized from ethanol to obtain 390 mg of ethyl α-(N-(2-furylmethyl))carbamoyl fluoroacetate, with a yield of 85%. The product was confirmed by NMR analysis, 1 H NMR (CDCl 3 ,500MHz,δ / ppm):7.36-7.35(m,1H);6.73(br,1H),6.32-6.31(m,1H);6.26-6.25(m,1H),5.26(d,J=48.5Hz ,1H),4.55-4.42(m,2H),4.36-4.26(m,2H),1.32(t,J=7.3Hz,3H).

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Abstract

The invention discloses a method for synthesizing an alpha-amine formyl fluoroacetate compound. The method comprises the steps: performing reaction on a primary amino compound and fluoro-malonate which serve as raw materials under a solvent-free condition to prepare the alpha-amine formyl fluoroacetate compound; or performing reaction on a primary amine acid salt compound and the fluoro-malonic ester in the presence of a solvent and an acid-binding agent to prepare the alpha-amine formyl fluoroacetate compound. The method is easy to operate, quick in response and high in yield, can solve the problem that alpha-amine formyl fluoroacetate compound cannot be conveniently and quickly synthesized, and is suitable for easy preparation in a laboratory. The compound disclosed by the invention can be used for synthesizing fluorine-containing organic molecules.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical and pesticide intermediates, in particular to a method for synthesizing α-carbamoyl fluoroacetate compounds. Background technique [0002] Fluorine-containing multifunctional compounds have been widely used in many fields such as medicine, pesticides and materials because of their special physical and chemical properties. α-carbamoyl fluoroacetate compounds, as a class of synthetic building block molecules with potential application prospects, are very convenient for the synthesis of fluorine-containing cyclic compounds and the construction of other fluorine-containing chiral center compounds. At present, there is no systematic synthesis research on such compounds in the literature, and the conventional synthesis method of amides (Amino Acids & Biotic Resources. 2010, 32(1): 34-38) is not only cumbersome to operate, but also takes a long time to react, and produces rate is not high. C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/06C07C231/02C07C233/05C07D307/52C07C233/06
Inventor 王伦林双政李秉擘王月梅杨翠凤武宗凯卫天琪
Owner XIAN MODERN CHEM RES INST
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