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Method for synthesis of L-norvaline

A synthesis method and technology of norvaline, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as difficulty in meeting production needs, achieve low cost, large output, and simple production process

Inactive Publication Date: 2007-05-16
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The existing synthesis method of L-norvaline is seldom seen in the report. The patent JP7553587 adopts the fermentation method to prepare, and the yield is about 3.7g / L, which is far lower than the yield of amino acid produced by general fermentation, and it is difficult to meet the needs of industrial production.
At present, the chemical synthesis method of this substance is only reported in Chinese patent CN1651400, but the method of this patent uses highly toxic acetone cyanohydrin as the reaction raw material, which has its limitations

Method used

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  • Method for synthesis of L-norvaline
  • Method for synthesis of L-norvaline
  • Method for synthesis of L-norvaline

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Embodiment 1

[0020] Embodiment 1: A kind of synthetic method of L-norvaline, take n-valeric acid as main starting material, make through following steps successively:

[0021] (1) Acyl chloride, i.e. the preparation of n-pentanoyl chloride:

[0022] In the flask equipped with stirring, reflux condenser, dropping funnel, calcium chloride drying tube and thermometer, add n-valeric acid (36.7g, 0.36mol) and thionyl chloride (123.9g, 1.04mol) successively, oil Bath heating, reflux at 78 ° C for 4 hours, until no hydrogen chloride gas is released.

[0023] (2) bromination, preparation of α-bromovaleryl chloride:

[0024] Keep the liquid obtained in the previous step slightly boiling, and the reaction temperature is 80°C. Liquid bromine (60.5 g, 0.38 mol) dried with an equal volume of concentrated sulfuric acid is added dropwise to the flask, and the dropping process is completed within 5 hours. After the dropwise addition was completed, heating and stirring were stopped, and the mixture was a...

Embodiment 2

[0034] Embodiment 2: a kind of synthetic method of L-norvaline, take n-valeric acid as main starting material, make through following steps successively:

[0035] (1) Acyl chloride, i.e. the preparation of n-pentanoyl chloride:

[0036] In the flask equipped with stirring, reflux condenser, dropping funnel, calcium chloride drying tube and thermometer, add n-valeric acid (36.7g, 0.36mol) and thionyl chloride (42.9g, 0.36mol) successively, oil Bath heating, reflux at 50 ° C for 8 hours, until no hydrogen chloride gas is released.

[0037] (2) bromination, preparation of α-bromovaleryl chloride:

[0038] Keeping the temperature of the liquid obtained in the previous step at 50°C, liquid bromine (115.2 g, 0.72 mol) dried with an equal volume of concentrated sulfuric acid was added dropwise to the flask, and the dropping process was completed within 1 h. After the dropwise addition was completed, heating and stirring were stopped, and the mixture was allowed to stand overnight. ...

Embodiment 3

[0048] Embodiment 3: a kind of synthetic method of L-norvaline, take n-valeric acid as main starting material, make through following steps successively:

[0049] (1) Acyl chloride, i.e. the preparation of n-pentanoyl chloride:

[0050] In the flask equipped with stirring, reflux condenser, dropping funnel, calcium chloride drying tube and thermometer, add n-valeric acid (36.7g, 0.36mol) and thionyl chloride (214.4g, 1.80mol) successively, water bath React at 10°C for 1h.

[0051] (2) bromination, preparation of α-bromovaleryl chloride:

[0052] Keeping the temperature of the liquid obtained in the previous step at 65°C, liquid bromine (86.4 g, 0.54 mol) dried with an equal volume of concentrated sulfuric acid was added dropwise to the flask, and the dropping process was completed within 10 h. After the dropwise addition was completed, the stirring was stopped and left to stand overnight. The next day, rectification under reduced pressure collected 64.0 g of 88-90°C / 9mmHg f...

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Abstract

The invention discloses a synthesizing method of L-norvaline based on valerianic acid as raw material, which comprises the following steps: 1) proceeding acylated chloride reaction for valerianic acid acted by sulfone chloride to obtain valeryl chloride; 2) reacting valeryl chloride and liquid bronmine; removing sulfone chloride and bromine to obtain the rough product of alpha-bromovaleryl chloride; 3) dissolving alpha-bromovaleryl chloride in the solvent to ammonolyze; washing; condensing to obtain racemic alpha-aminovaleramide; 4) detaching the racemic alpha-aminovaleramide to obtain L-aminovaleramide tartrate; 5) recrystallizing; 6) hydrolyzing.

Description

technical field [0001] The invention relates to a method for synthesizing an organic compound, in particular to a method for synthesizing an amino acid—L-norvaline. Background technique [0002] [0003] L-norvaline with the molecular formula shown in S-1 is a key intermediate for the synthesis of the drug perindopril (the molecular formula shown in S-2). The existing synthesis method of L-norvaline is seldom seen in the report, and the patent JP7553587 adopts the fermentation method to prepare, and the output is about 3.7g / L, far lower than the output of general fermentation amino acid production, it is difficult to meet the production needs of industrialization. At present, the chemical synthesis method of this substance is only reported in Chinese patent CN1651400, but the method of this patent uses highly toxic acetone cyanohydrin as a reaction raw material, which has its limitations. Contents of the invention [0004] Aiming at the technical problems existing in t...

Claims

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Application Information

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IPC IPC(8): C07C229/08C07C227/06C07C227/12
Inventor 陈新志钱超
Owner ZHEJIANG UNIV
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