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Synthesis method of L-n-valaine

A synthesis method and technology of norvaline, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems that it is difficult to meet the production needs, and the chemical synthesis method has not been used yet, and achieves small investment, The effect of convenient production and simple production process

Inactive Publication Date: 2005-08-10
王旭
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  • Summary
  • 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 has not been used yet.

Method used

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  • Synthesis method of L-n-valaine
  • Synthesis method of L-n-valaine

Examples

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Embodiment 1

[0019] Embodiment 1: a kind of synthetic method of L-norvaline, take n-butyraldehyde and acetone cyanohydrin as main starting raw material, make through following steps successively:

[0020] (1) cyanation, i.e. the preparation of butyraldehyde cyanohydrin:

[0021] Acetone cyanohydrin (8.5 g, 0.1 mol) was cooled to 0°C, and 10% methanolic potassium hydroxide solution was added dropwise with stirring until the pH value was about 8 and stopped. Control the temperature at 5-10°C, add n-butyraldehyde (7.92g, 0.11mol) dropwise within 20min, keep the temperature and react for 15h after the dropwise addition is complete (take the reaction solution at this time for GC analysis, the content of acetone cyanohydrin <1% , n-butyraldehyde content<3%); after the reaction, add phosphoric acid for neutralization, and adjust the pH value to 3-3.3. The reaction solution was filtered, and the filtrate was concentrated and used directly for the next step of synthesis.

[0022] (2) ammoniation,...

Embodiment 2

[0032] Embodiment 2: a kind of synthetic method of L-norvaline, take n-butyraldehyde and acetone cyanohydrin as main starting raw material, make through following steps successively:

[0033] (1) cyanation, i.e. the preparation of butyraldehyde cyanohydrin:

[0034] Acetone cyanohydrin (8.5 g, 0.1 mol) was cooled to 0° C., and 10% methanolic potassium hydroxide solution was added dropwise with stirring until the pH value was about 7 and stopped. Control the temperature at 10-15°C, add n-butyraldehyde (14g, 0.19mol) dropwise within 20min, keep the temperature for 10h and stop after the dropwise addition; after the reaction, add phosphoric acid for neutralization and adjust the pH value to 3-3.3. The reaction solution was filtered, and the filtrate was concentrated and used directly for the next step of synthesis.

[0035] (2) ammoniation, i.e. the preparation of aminovaleronitrile:

[0036] Add liquid ammonia (11.9 g, 0.7 mol) into the autoclave, press butyraldehyde cyanohydr...

Embodiment 3

[0045] Embodiment 3: a kind of synthetic method of L-norvaline, take n-butyraldehyde and acetone cyanohydrin as main starting raw material, make through following steps successively:

[0046] (1) cyanation, i.e. the preparation of butyraldehyde cyanohydrin:

[0047] Acetone cyanohydrin (8.5 g, 0.1 mol) was cooled to 0° C., and 10% methanolic sodium hydroxide solution was added dropwise with stirring until the pH value was about 9 and stopped. Control the temperature at 0-5°C, add n-butyraldehyde (10.8g, 0.15mol) dropwise within 20min, keep the temperature and react for 5h after the dropwise addition is completed; add phosphoric acid to neutralize after the reaction, adjust the pH value to 3-3.3 . The reaction solution was filtered, and the filtrate was concentrated and used directly for the next step of synthesis.

[0048] (2) ammoniation, i.e. the preparation of aminovaleronitrile:

[0049] Add liquid ammonia (15.3 g, 0.9 mol) into the autoclave, press butyraldehyde cyanoh...

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Abstract

A process for synthesizing L-valine from n-butanol and acetone cyanohydrin includes cyanation reacting under action of alkaline catalyst to obtain butanol cyanohydrin, ammonifying reacting on liquid ammonia, deammonifying, dewatering to obtain aminopentylonitrile, hydrolyzing in concentrated sulfuric acid, neutralizing, extracting, concentrating to obtain dl-aminopentyl amide, splitting, recrystallizing, dissolving in water, ion exchanging by cationic exchange resin, eluting by ammonia water, decoloring, dewatering, rinsing and drying.

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 has not been used yet. Contents of the invention [0004] Aiming at the technical problems existing in the prior art, the invention provides an environment-friendly, simple process and low-cost L-norvaline synthesis method. [0005] In order to achi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/00C07C229/08
Inventor 王旭
Owner 王旭
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