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Optical activity alpha-amino acid and preparation of derivative thereof

A technology of alkyl and benzyl, which is applied in the field of preparing optically active α-amino acid and α-amino acid derivatives, and can solve the problem of not being able to obtain optically active amino acids

Inactive Publication Date: 2008-04-23
WUHAN ENDEHUA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the patent DE19833853 has made some improvements to the method of the patent WO9710203 and overcomes some of the shortcomings of the patent WO9710203, the most fundamental problem has not been solved: the final hydrolysis reaction can only obtain the amino acid formamide, and cannot obtain the really required optical activity. amino acids

Method used

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  • Optical activity alpha-amino acid and preparation of derivative thereof
  • Optical activity alpha-amino acid and preparation of derivative thereof
  • Optical activity alpha-amino acid and preparation of derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1R2

[0162] Example 1R2, R4, R5 is the preparation of H imidazolinone 2, that is, the synthesis of 1,4-diazaspiro[4,5]decan-2-one

[0163] 40 millimoles of cyclohexanone and equimolar glycamide hydrochloride were refluxed in a mixture of methanol and triethylamine for 40 hours. After evaporating the solvent to dryness, the resulting residue was dissolved in ethyl acetate and water, and the aqueous layer was separated and extracted twice more with ethyl acetate. The organic layers were combined, washed with water, saturated brine, and dried over anhydrous sodium sulfate. After removing the desiccant, evaporate to dryness under reduced pressure to obtain white solid product #1 (1,4-diazaspiro[4,5]decan-2-one). (See Table 1)

[0164] Example 2R2 is H, R4 is isopropyl, and R5 is the synthesis of methyl imidazolinone, that is, the synthesis of (5S, 6S, 9R)-6-isopropyl-9-methyl-1, 4-diazaspiro [4,5 ]decan-2-one)

[0165] 10 millimoles of L-menthone and equimolar glycamide hydrochlori...

example 4

[0171] Example 4 prepares nitrone compound (R2, R4, R5 is H),

[0172] That is, the synthesis of 1,4-diazaspiro[4,5]decan-3-one-1-oxide

[0173]20 millimoles of compound #1 obtained in Example 1 were dissolved in 300 milliliters of dichloromethane, and 50 millimoles of 70% m-chloroperoxybenzoic acid were added several times under the cooling reaction condition in an ice-water bath. Stirring was continued at this temperature for 3 hours after the addition was complete. Excess m-chloroperoxybenzoic acid was eliminated with aqueous sodium sulfite and washed with saturated sodium bicarbonate solution until no gas evolved. The aqueous layer was extracted twice with dichloromethane, and all the collected organic layers were washed once with saturated brine and dried over anhydrous sodium sulfate. After filtration to remove sodium sulfate, evaporation to dryness gave the product #3 as a white solid. (See Table 2)

example 5

[0174] Example 5 prepares nitrone compounds (R2 is H, R4 is isopropyl, R5 is methyl), that is, synthesis of (5R, 6S, 9R)-6-isopropyl-9-methyl-1, 4-diazaspiro [4, 5] decan-3-one-1-oxide

[0175] The #2 compound (prepared by L-menthone) obtained in the example 2 of 10 millimoles is dissolved in 200 milliliters of methylene chloride, under the cooling reaction condition of ice-water bath, divide and add 30 millimoles of 70 % m-chloroperoxybenzoic acid. Stirring was continued at this temperature for 3 hours after the addition was complete. Excess m-chloroperoxybenzoic acid was eliminated with aqueous sodium sulfite and washed with saturated sodium bicarbonate solution until no gas evolved. The aqueous layer was extracted twice with dichloromethane, and all the collected organic layers were washed once with saturated brine and dried over anhydrous sodium sulfate. After filtering off the sodium sulfate, it was evaporated to dryness to give the product #4 as a white solid. (See T...

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Abstract

The present invention provides one kind of compound for preparing optically active alpha-amino acid and alpha-amino acid derivative and its preparation process. The present invention also provides economic reasonable effective process of synthesizing optically active alpha-amino acid and alpha-amino acid derivative.

Description

technical field [0001] The present invention relates to the preparation method of amino acid and derivatives thereof, in particular to a new method for preparing optically active α-amino acid and α-amino acid derivatives. Background technique [0002] Amino acids are a class of biologically active compounds. Among them, natural amino acid is the main component of protein and an important building block of life. Non-protein amino acids are not involved in building proteins and do not belong to the list of 20 amino acids. In recent years, non-protein amino acids have been more and more widely used in biologically active peptides, such as in the research of new drugs. Utilizing its special properties, it promotes and inhibits the biological activity of certain enzymes in the body to achieve good effects in treating diseases. Therefore, it is very important to develop new methods for amino acid synthesis and prepare new amino acids. [0003] Among the literature reports on t...

Claims

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Application Information

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IPC IPC(8): C07D235/00
Inventor 成尚理
Owner WUHAN ENDEHUA TECH
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