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Method for synthesizing beta-amino acid

A technology of amino acid and benzyl, applied in the field of synthesizing β-amino acid, achieving high yield, simple method and mild reaction conditions

Active Publication Date: 2009-09-09
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] This method is suitable for the synthesis of various β-amino acids, especially for the synthesis of aliphatic β-amino acids that cannot be easily prepared by existing literature methods

Method used

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  • Method for synthesizing beta-amino acid
  • Method for synthesizing beta-amino acid

Examples

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Embodiment 1

[0025] Synthesis of 3-amino-pentanoic acid

[0026] 1. Put 1.0 mol of n-propionaldehyde and 1.0 mol of malonic acid into a 2L three-necked reaction flask, add 1L of pyridine to dissolve, and then add 0.1 mol of diethylamine; keep the temperature at 30℃ and react for 12 hours, heat up to 50℃ for 24 hours Hours; then add 1.0 mol benzylamine, heat up to 130° C. and react for 8 hours. After cooling, the product precipitates out of the system, and suction filtration obtains 3-benzylaminovaleric acid (light yellow to white solid), with a yield of 75%.

[0027] 2. Dissolve 1.0 mol of 3-benzylaminovaleric acid in a 1L methanol and water mixed system, add 5.0% (Wt%) palladium / carbon, add hydrogen, and react at 1 atm for 48 hours. After filtering off the palladium carbon, The mother liquor was evaporated to dryness to obtain a pale yellow to white solid with a yield of 99%.

Embodiment 2

[0029] Synthesis of 3-Amino-4-methyl-pentanoic acid

[0030] 1. Put 1.0 mol of isopropanal and 1.0 mol of malonic acid into a 2L three-necked reaction flask, add 1L of pyridine to dissolve, and then add 0.1 mol of diethylamine; keep the temperature at 45℃ and react for 12 hours, and heat up to 60℃ for 24 hours Hours; then add 1.0 mol of benzylamine, heat up to 130° C. and react for 8 hours. After cooling, the product precipitates out of the system, and suction filtration obtains 3-benzylamino isobutyric acid (light yellow to white solid) with a yield of 75%.

[0031] 2. Dissolve 1.0 mol of 3-benzylaminoisobutyric acid in a mixed system of 1L methanol and water, add 5.0% (Wt%) palladium / carbon, add hydrogen, and react at 1atm for 48 hours. After filtering off the palladium-carbon , The mother liquor is evaporated to dryness to obtain a pale yellow to white solid with a yield of 99%.

Embodiment 3

[0033] Synthesis of 3-Amino-hexanoic acid

[0034] 1. Put 1.0 mol of n-butyraldehyde and 1.0 mol of malonic acid into a 2L three-necked reaction flask, add 1L of pyridine to dissolve, and then add 0.1 mol of diethylamine; keep the temperature at 30℃ and react for 12 hours, heat up to 50℃ for 24 hours Hours; then add 1.0 mol of benzylamine, increase the temperature to 130° C. and react for 8 hours. After cooling, the product precipitates out of the system, and suction filtration obtains 3-benzylaminohexanoic acid (light yellow to white solid) with a yield of 73%.

[0035] 2. Dissolve 1.0 mol of 3-benzylaminohexanoic acid in a 1L methanol and water mixed system, add 5.0% (Wt%) palladium on carbon, pass in hydrogen, react at 3.0 atm for 24 hours, and then process, filter out the palladium After carbon, the mother liquor was evaporated to dryness to obtain a pale yellow to white solid with a yield of 94%.

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Abstract

The invention relates to a method for synthesizing beta-amino acid. Under the condition that aldehyde, malonic acid and benzyl amine are in one pot, N-benzyl beta-amino acid is obtained with high yield by controlling the reaction condition; and the N-benzyl beta-amino acid is converted into free beta-amino acid under the catalysis of palladium and carbon. The method has the advantages of convenience, simple operation, mild reaction condition and high yield, and is easy to achieve industrialized production. The invention provides a novel method for industrialized production of beta-amino acid.

Description

Technical field [0001] The invention relates to a method for synthesizing β-amino acids, which belongs to the field of organic synthesis. Background technique [0002] β-amino acids are widely used in organic synthesis, pesticides, medicine and other fields. It is an important intermediate for many foreign drugs that have been on the market or are ready to be marketed. Such as: Deoxynegamycin, an antibacterial drug developed by Vicuron Pharmaceuticals; Aspoxicillin, an antibiotic developed by Merck KGaA for the treatment of gastrointestinal diseases; Merck Pharmaceuticals’ latest type II diabetes drug Sitagliptin; and an antitumor drug BMS- 200532, Paclitaxel-SNO, a cardiovascular drug developed by NitroMed, etc. [0003] There are many types of β-amino acid synthesis methods, and the more common methods are as follows: [0004] a. Rodionow; (Izv. Akad. Nauk SSSR Ser. Khim.; 1945; 233) and others found that the direct reaction of fatty aldehyde, malonic acid and ammonia ethanol s...

Claims

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Application Information

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IPC IPC(8): C07C229/08C07C229/34C07C229/30C07C227/18C07C227/10
Inventor 孙绍光郭鹏黄纯敬胡勋伍睿
Owner ASTATECH CHENGDU BIOPHARM CORP
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