Beta-aminophosphonic acid derivative and preparation method thereof

An aminophosphonic acid and derivative technology, which is applied in the field of preparation of organic compounds, can solve the problems of harsh reaction conditions, difficult to obtain raw materials, and many reaction steps, and achieves the effects of mild reaction conditions, few steps, and high yield.

Active Publication Date: 2018-11-02
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] However, the prior art has the following problems: an equivalent amount of metal lithium reagent and sodium borohydride reducing agent are required, the reaction conditions are harsh, and there are many reaction steps; the raw materials are difficult to obtain, the reaction steps are many, and the yield is low; expensive cyanoborohydrogenation is required Sodium as reducing agent, lower yield

Method used

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  • Beta-aminophosphonic acid derivative and preparation method thereof
  • Beta-aminophosphonic acid derivative and preparation method thereof
  • Beta-aminophosphonic acid derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Synthesis of 2-amino-1-phenylethylphosphonic acid

[0045] With N-(styryl) benzamide as raw material, the reaction steps are as follows:

[0046] (1) Add N-(styryl)benzamide (223 mg, 1 mmol), dimethyl phosphite (220 mg, 2 mmol), manganese acetate (580 mg, 2.5 mmol) into the reaction flask, anhydrous Potassium carbonate (276 mg, 2 mmol) and methanol (10 mL). The mixture was stirred and reacted at room temperature, followed by TLC until the reaction was completely completed (about 0.5 hours);

[0047] (2) The crude product obtained after the reaction finishes is separated by column chromatography (dichloromethane: methanol=100:1) to obtain (2-benzamido-1-styryl) dimethylphosphonate (281 mg, 0.85 mmol, 85% yield). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 8.19 – 8.06 (m, 2H), 7.64 – 7.60 (m, 2H), 7.52(dd, J = 15.0, 7.5 Hz, 3H), 7.45 – 7.37 (m, 5H), 3.78 (s, 3H), 3.75 (s, 3H).

[0048] (3) The above product (2-benz...

Embodiment 2

[0051] Example 2: Synthesis of 2-amino-1-(2-tolyl)ethylphosphonic acid

[0052] With N-(2-methylstyryl) benzamide as raw material, the reaction steps are as follows:

[0053] (1) Add N-(2-methylstyryl)benzamide (237 mg, 1 mmol), dimethyl phosphite (220 mg, 2 mmol), manganese acetate (580 mg, 2.5 mmol), anhydrous potassium carbonate (276 mg, 2 mmol) and methanol (10 mL). The mixture was stirred and reacted at room temperature, followed by TLC until the reaction was completely completed (about 0.5 hours);

[0054] (2) The crude product obtained after the reaction is separated by column chromatography (dichloromethane:methanol=100:1) to obtain (2-benzamido-1-(2-tolyl)vinyl)dimethyl Phosphonate (280 mg, 0.81 mmol, 81% yield). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 8.19–8.06 (m, 2H), 7.70–7.50 (m, 3H), 7.40–6.80 (m, 4H), 3.78 (s, 3H), 3.75 (s, 3H) , 1.75 (s, 3H);

[0055] (3) Add the above product (280 mg, 0.81 mmol), Raney-Ni (56.4 m...

Embodiment 3

[0057] Example 3: Synthesis of 2-amino-1-(2-methoxyphenyl)ethylphosphonic acid

[0058] With N-(2-methoxy styryl) benzamide as raw material, the reaction steps are as follows:

[0059] (1) Add N-(2-methoxystyryl)benzamide (253 mg, 1 mmol), dimethyl phosphite (220 mg, 2 mmol), manganese acetate (580 mg, 2.5 mmol), anhydrous potassium carbonate (276 mg, 2 mmol) and methanol (10 mL). The mixture was stirred and reacted at room temperature, followed by TLC until the reaction was completely completed (about 0.5 hours);

[0060] (2) The crude product obtained after the reaction is separated by column chromatography (dichloromethane:methanol=100:1) to obtain (2-benzamido-1-(2-methoxyphenyl)vinyl) Dimethylphosphonate (289 mg, 0.80 mmol, 80% yield). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 8.21–8.01 (m, 2H), 7.70–7.50 (m, 4H), 7.40–6.80 (m, 5H), 3.79 (s, 3H), 3.77 (s, 3H), 3.74 (s, 3H);

[0061] (3) Add the above product (289 mg, 0.80 mmo...

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Abstract

The invention discloses a preparation method of a beta-aminophosphonic acid derivative. The preparation method comprises the following steps of dissolving N-(arylvinyl)benzamide, dialkyl phosphite, manganese acetate and potassium carbonate in a solvent, performing reaction at a room temperature to acquire a (2-benzamido-1-arylvinyl)dialkyl phosphonate derivative, and performing reductive hydrolyzation on a compound to acquire the beta-aminophosphonic acid derivative. By using an N-(arylvinyl)benzamide derivative as an initiator, the preparation method is available in raw material and various in preparation method. The preparation method is simple and short in synthetic route, mild in reaction condition, simple in reaction operation and aftertreatment process and better in yield and is suitable for scale production.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a preparation method of β-aminophosphonic acid derivatives. Background technique [0002] β-Aminophosphonic acid derivatives have a wide range of physiological activities, such as antibacterial, nerve stimulating, affecting cell growth and metabolism, pain relief, regulating blood pressure, regulating plant growth, etc., so they can be used as medicine, pesticide, antagonist, anthocyanin Synthetic inhibitors, fructose bisphosphatase inhibitors, etc. (see: Maier, L. Phosphorus Sulfur 1983, 14, 295; Abbenante, Giovanni; Australian J. Chem. , 1997, 50, 523-527). [0003] In the prior art, the synthetic methods of β-aminophosphonic acid derivatives mainly contain the following types: [0004] [0005] [0006] [0007] [0008] However, the prior art has the following problems: an equivalent amount of metal lithium reagent and sodi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/38
CPCC07F9/38
Inventor 邹建平张栋梁李成坤张国玉陶泽坤
Owner SUZHOU UNIV
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