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Process for synthesizing beta-amino acid using ketone as raw material

A technology of amino acids and raw materials, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as difficult product separation and purification, high cost, unsafe operation, etc., achieve cheap raw materials, increase diversity, and synthesize Effects in simple steps

Inactive Publication Date: 2004-07-14
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The object of the present invention is to provide a ketone starting from abundant sources and cheap price in order to overcome the defects of limited product diversity, high cost, unsafe operation and difficulty in product separation and purification in order to overcome the limited source of raw materials in the above method. Synthetic method of β-amino acid with simple raw materials and operation steps and industrial production

Method used

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  • Process for synthesizing beta-amino acid using ketone as raw material
  • Process for synthesizing beta-amino acid using ketone as raw material
  • Process for synthesizing beta-amino acid using ketone as raw material

Examples

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Embodiment 1

[0076] Embodiment 1 (malonic acid method)

[0077] Preparation of β-substituted β-amino acids from cyclohexanone: 1-aminocyclohexyl-acetic acid

[0078] Put a large stirring magnet in a 500 ml round bottom bottle, add 49.0 g of malonic acid (molecular weight 104.06, 0.47 mol), 50.8 g of ammonium acetate (molecular weight 77.08, 0.66 mol) and 116 ml of hot ethanol, install and condense tube, heated to reflux with stirring on an oil bath at 100°C, and added 55 ml of cyclohexanone (specific gravity 0.947, 52.11 g; molecular weight 98.14, 0.53 mol). The reactant gradually dissolves and a large number of bubbles are released. The reaction liquid starts to be yellow, and the color gradually deepens as the reaction progresses, from yellow to deep yellow, yellowish brown, and finally brown. After 8 hours of reaction, the heating was stopped, and the reaction device was changed to a distillation device, and about half of the solvent was evaporated under reduced pressure, and cooled to...

Embodiment 2

[0080] Embodiment 2 (ethyl cyanoacetate method)

[0081] Preparation of α-substituted β-amino acids from cyclohexanone: 2-cyclohexyl-3-amino-propionic acid

[0082] (1) Preparation of enester: 103 milliliters of cyclohexanone (specific gravity 0.947, 97.5 grams; molecular weight 98.14, 0.99 moles) and 100 milliliters of ethyl cyanoacetate (specific gravity 1.061, 106.1 grams; molecular weight 113.12, 0.94 moles) were added to the flask In the mixture, add 3 milliliters of diethylamine dropwise under stirring, and leave it for 48 hours (it must be left for a long enough time, and turbidity can be observed, which is the reason for the reaction to produce water). Then add 100 milliliters of water to the reaction system, separate the oil layer, then wash the oil layer in the separatory funnel with water, dry the oil layer, and obtain the oily thing that is 50 grams of enester (molecular weight 193.24, 0.26 mole), and the condensation yield is 27.7%.

[0083] (2) Catalytic hydrog...

Embodiment 3

[0091] Embodiment 3 (cyanoacetic acid method)

[0092] Preparation of α-substituted β-amino acids from cyclohexanone: 2-cyclohexyl-3-amino-propionic acid

[0093] (1) Preparation of enoic acid: 57 milliliters of cyclohexanone (specific gravity 0.947, 54 grams; molecular weight 98.14, 0.54 moles), 42.5 grams of cyanoacetic acid (molecular weight 85.16, 0.50 moles), 2 grams of ammonium acetate and 100 milliliters of benzene were added Then add 100 ml of benzene to the reaction system, transfer it to a separatory funnel, add 200 ml of ether, and wash with water twice (except ammonium acetate); the oil layer is distilled Ethyl ether and benzene were removed, and the residue was solidified and washed with benzene or petroleum ether to obtain a white solid, enoic acid, weighing 35 grams (molecular weight: 165.19, 0.21 mol), with a yield of 42%.

[0094] (2) Catalytic hydrogenation reaction

[0095] (a) Double bond reduction

[0096] At room temperature, in a reactor, the 35 gram ...

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Abstract

The present invention relates to the process of synthesizing beta-amino acid with ketone as raw material, and the process may be malonic acid process, ethyl cyanoacetate process or cyanoacetic acid process. The malonic acid process produces beta-amino acid through reaction of ketone, malonic acid and ammonium acetate inside alcohol medium and at reflux temperature. The ethyl cyanoacetate process produces beta-amino acid through condensation of ketone and ethyl cyanoacetate to synthesize alkenyl ester, hydrogenation reducing double bond of alkenyl ester with Pd-C as catalyst, hydrogenation reducing cyano group of alkenyl ester with Raney Ni as catalyst, and final hydrolysis. The cyanoacetic acid process produces beta-amino acid through condensation of ketone and cyanoacetic acid to synthesize olifine acid, hydrogenation reducing double bond of olifine acid with Pd-C as catalyst, and hydrogenation reducing cyano group of olifine acid with Raney Ni as catalyst.

Description

technical field [0001] The invention belongs to the technical field of synthesizing unnatural amino acids, in particular to a method for synthesizing β-amino acids with ketones as raw materials. Background technique [0002] For a long time, β-amino acids and their derivatives have received extensive attention due to their biological activities and important applications in the pharmaceutical field. A.F.Spatolade et al. wrote "Biochemistry of Amino Acids" (Hall, London, 1985) in 1985, on page 25 of the third chapter, it is believed that the introduction of β-amino acids at a certain position in the polypeptide can improve its stability to proteases, and Can improve its biological activity. In recent years, B.L. Iverson discovered the secondary helical structure of β-polypeptide on page 113 of volume 385 of "Nature" magazine in 1997, which further aroused people's interest in the research of β-amino acids. It is expected that β-amino acids will become...

Claims

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Application Information

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IPC IPC(8): C07C227/00C07C227/04C07C229/04C07C229/08
Inventor 沈涛王小兵宋爱民张曼华周亚琳
Owner INST OF CHEM CHINESE ACAD OF SCI
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