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New method for synthesizing non-natural product beta-amino acid

An amino acid and non-natural technology, which is applied in the preparation of organic compounds, chemical instruments and methods, and the production of bulk chemicals. It can solve the problems of high synthesis cost, low safety, and many steps, and achieve simple operation and high safety. , less side effects

Active Publication Date: 2015-10-21
JIANGXI SCI & TECH NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to overcome the problems of many steps, high toxicity, low safety and high synthesis cost in the existing unnatural beta-amino acid synthesis method, and provide a new synthetic process route for the synthesis of unnatural beta-amino acid

Method used

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  • New method for synthesizing non-natural product beta-amino acid
  • New method for synthesizing non-natural product beta-amino acid
  • New method for synthesizing non-natural product beta-amino acid

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Embodiment 1

[0023] 1) synthesis of formula 2 compound

[0024] At 0°C, 4-piperidin-1-one (3.0 g, 30.26 mmol) was dissolved in 100 mL of dry dichloromethane, under nitrogen protection, triethylamine (21 mL, 151.32 mmol) was added, and stirred for 30 minutes , the temperature was raised to normal temperature, then di-tert-butyl dicarbonate (9.91g, 45.39mmol) was dissolved in 20mL of dry dichloromethane, then the mixture was slowly added to the reaction flask, stirred overnight, and detected by point plate The reaction is completely over. Afterwards, stop the reaction with saturated ammonium chloride aqueous solution, then extract with dichloromethane (3×150mL), combine the organic phases, add saturated sodium chloride solution to wash, dry over anhydrous sodium sulfate, filter, and evaporate the solvent under reduced pressure, The compound of formula 2 was isolated by silica gel column chromatography as a white solid (5.91 g) with a yield of 98%.

[0025] 2) Synthesis of formula 3 compoun...

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Abstract

The invention discloses a new method for synthesizing non-natural product beta-amino acid. 4-piperidine-1-ketone is taken as the basic raw material, after being subjected to dimethyl carbonate tert-butyl ester amino protection and lithium diisopropylamide hydrogen-pulling, the 4-piperidine-1-ketone is subjected to a reaction with chlorine formic acid allyl ester, an alkylation reaction under an alkaline condition, an asymmetric decarboxylation reaction of beta-carbonyl allyl acetate under metal catalysis, an Saegusa oxidation reaction, sodium periodate oxidation cutting-off and protecting group removal, and then the non-natural product beta-amino acid is obtained. According to the new method for the synthesizing non-natural product beta-amino acid, the synthesizing route design is unique and novel, the raw material source is easy to obtain, and the raw material cost is low, the toxicity is low, the operation is simple and convenient, the high enantioselectivity, the high yield and the good repeatability of the beta-amino acid products are achieved, the reaction process is gentle in conditions, high in safety and less in side reactions, the cost is greatly reduced, and realization of industrialization and industrial production of the non-natural product beta-amino acid is facilitated.

Description

technical field [0001] The invention relates to a synthetic method of unnatural products, in particular to a new method for synthesizing unnatural beta-amino acids. Background technique [0002] Natural products containing unnatural beta-amino acid structures (such as paclitaxel) have shown good anticancer or antibacterial biological activities. In 2007, the research group of Professor Schepartz of Yale University found that the polypeptide composed of beta-amino acids can also form a helical structure similar to natural alpha-amino acid polypeptides, and has a folding conformation similar to natural proteins. [0003] Different from natural alpha-amino acids, after long-term evolutionary selection in nature, the content of unnatural beta-amino acids in natural polypeptides, proteins and other basic life substances is very low. However, beta-amino acids play a very important role in the regulation and metabolism of living organisms. This has a lot to do with its unique che...

Claims

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Application Information

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IPC IPC(8): C07C229/08C07C227/20C07C227/32
CPCY02P20/55
Inventor 王晓季冯俊敏王李平黄双平孙猛林爽杰刘帅
Owner JIANGXI SCI & TECH NORMAL UNIV
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