L-norvaline preparation method

A technology of norvaline and n-valeric acid is applied in the preparation of carboxylate, carboxylic acid amide, preparation of organic compounds, etc., can solve problems such as large limitations, and achieve the effect of meeting production needs

Inactive Publication Date: 2019-12-31
ABA CHEM NANTONG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the deficiencies of the prior art, the present invention provides a preparation method of L-norvaline, which has the advantages of simple production process, etc., and solves the problem of using highly toxic acetone cyanohydrin as the reaction raw material and having large limitations.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment one: a kind of preparation method of L-norvaline, comprises the following steps:

[0024] 1) Acyl chloride: clean and dry the reactor, put in thionyl chloride, start stirring and add n-valeric acid, control the reaction temperature to 20°C, and control the reaction time to 2 hours to obtain n-valeryl chloride.

[0025] 2) Bromination: react the obtained n-valeryl chloride with liquid bromine to obtain a reaction liquid, control the reaction temperature to 55° C., control the reaction time to 2 h, and carry out the step of removing thionyl chloride and bromine from the obtained reaction liquid, Carry out distillation and collect fractions to obtain a colorless to light yellow transparent liquid, which is the crude product of α-bromo-n-valeryl chloride, and the reaction yield is over 90%.

[0026] 3) Ammonification: Add liquid ammonia into the autoclave, start stirring and add the crude α-bromo-n-valeryl chloride obtained in the previous step, control the react...

Embodiment 2

[0030] Embodiment two: a kind of preparation method of L-norvaline, comprises the following steps:

[0031] 1) Acyl chloride: Clean and dry the reactor, put in thionyl chloride, start stirring and add n-valeric acid, control the reaction temperature to 80°C, and control the reaction time to 8 hours to obtain n-valeryl chloride.

[0032] 2) Bromination: react the obtained n-pentanoyl chloride with liquid bromine to obtain a reaction liquid, control the reaction temperature to 75°C, control the reaction time to 9h, and carry out the step of removing thionyl chloride and bromine from the obtained reaction liquid, Carry out distillation and collect fractions to obtain a colorless to light yellow transparent liquid, which is the crude product of α-bromo-n-valeryl chloride, and the reaction yield is over 90%.

[0033] 3) Ammonification: Add liquid ammonia into the autoclave, start stirring and add the crude α-bromo-n-valeryl chloride obtained in the previous step, control the reacti...

Embodiment 3

[0037] Embodiment three: a kind of preparation method of L-norvaline, comprises the following steps:

[0038] 1) Acyl chloride: clean and dry the reactor, put in thionyl chloride, start stirring and add n-valeric acid, control the reaction temperature to 50°C, and control the reaction time to 6 hours to obtain n-valeryl chloride.

[0039] 2) Bromination: react the obtained n-valeryl chloride with liquid bromine to obtain a reaction liquid, control the reaction temperature to 65° C., control the reaction time to 5 h, and carry out the step of removing thionyl chloride and bromine from the obtained reaction liquid, Carry out distillation and collect fractions to obtain a colorless to light yellow transparent liquid, which is the crude product of α-bromo-n-valeryl chloride, and the reaction yield is over 90%.

[0040] 3) Ammonification: Add liquid ammonia into the autoclave, start stirring and add the crude α-bromo-n-valeryl chloride obtained in the previous step, control the rea...

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PUM

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Abstract

The invention relates to the technical field of chemical synthesis, and discloses an L-norvaline preparation method, which comprises: 1) acyl chlorination: washing a reaction kettle, drying, adding thionyl chloride, starting stirring, adding n-valeric acid, and controlling the reaction temperature at 20-80 DEG C and the reaction time at 2-8 h to obtain n-valeryl chloride. According to the invention, thionyl chloride is fed, the thionyl chloride is decomposed into sulfur dioxide and hydrogen chloride or chlorinated hydrocarbon when meeting water or alcohol so as to provide the selective substitution effect on hydroxyl, the thionyl chloride is soluble in benzene, chloroform and carbon tetrachloride, is decomposed after being heated to 150 DEG C, and is completely decomposed at a temperatureof 500 DEG C to obtain n-valeryl chloride, liquid bromine reacts with the n-valeryl chloride, and has strong affinity with hydrogen, and the mixing is performed with organic matters to obtain racemicalpha-aminopentanamide, such that the yield is far higher than the yield of the amino acid produced by common fermentation, and the industrial production requirements can be met.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of L-norvaline. Background technique [0002] L-norvaline is a chemical substance with a molecular formula of C5H11NO2. L-norvaline is a white crystalline powder, soluble in hot water and dilute hydrochloric acid, insoluble in ethanol and ether, and is the key to the synthesis of various drugs intermediate. [0003] L-norvaline with molecular formula as shown in S-1 is a key intermediate for the synthetic drug perindopril (molecular formula as shown in S-2), and there are many ways to synthesize L-norvaline Various, the patent JP7553587 is prepared by fermentation, and the output is about 3.7g / L, but it is far lower than the output of amino acids produced by general fermentation, and it is difficult to meet the needs of industrial production. At present, according to Chinese patent CN 100352801 C, a kind of L-norvalamine The synthetic method of a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/20C07C229/08C07C231/20C07C231/02C07C237/06C07C51/62C07C53/50C07C51/60C07C53/42
CPCC07C51/60C07C51/62C07C227/20C07C231/02C07C231/20C07C229/08C07C237/06C07C53/50C07C53/42
Inventor 蒋信义刘汝章徐军张敏华
Owner ABA CHEM NANTONG
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