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Method for synthesizing D-valine

A synthetic method, valine technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve production limitations, difficulty in controlling the acidity of the split system, split yield and unstable product quality, etc. problems, to achieve the effect of low equipment requirements, less solvent and catalyst consumption, simple and safe unit operation

Active Publication Date: 2011-05-25
ABA CHEM SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method uses acidic water as a solvent, which is difficult to control the acidity of the split system, resulting in unstable split yield and product quality, and limited production.

Method used

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  • Method for synthesizing D-valine
  • Method for synthesizing D-valine

Examples

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Embodiment 1

[0029] 1.1 Preparation of 2-amino-3-methylbutyronitrile:

[0030] In a 1000ml flask, add 200g of 30% sodium cyanide aqueous solution, 86.4g of ammonium chloride, and 111g of 25% ammonia water, stir to dissolve the solid, cool to 0°C, add 100.4g of isobutyraldehyde dropwise, after the dropwise addition is complete, heat to 40°C and react for 5 hours. Extract three times with 600ml of dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, concentrate under reduced pressure at 35°C to remove the solvent, and the residual liquid is 119g of 2-amino-3-methylbutyronitrile, with a yield of 87.4%.

[0031] 1.2 Preparation of 2-amino-3-methylbutanamide:

[0032] In a 500ml flask, add 6.66g of sodium hydroxide, 250ml of methanol, and 30g of distilled water, stir to dissolve the solid, add 42.5g of 2-amino-3-methylbutyronitrile, cool to below 0°C, add 29g of acetone, and React at 0-5°C for 6 hours, concentrate under reduced pressure at 38°C to recover the solven...

Embodiment 2

[0041] 2.1 Preparation of 2-amino-3-methylbutyronitrile:

[0042] In a 5000ml flask, add 1000g of 30% sodium cyanide aqueous solution, 500g of ammonium chloride, and 600g of 25% ammonia water, stir to dissolve the solid, cool to 0°C, add 500g of isobutyraldehyde dropwise, after the dropwise addition is completed, heat to 40 °C, react for 5 hours. Extract three times with 3000ml of dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, concentrate under reduced pressure at 35°C to evaporate the solvent, the residual liquid is 578g of 2-amino-3-methylbutyronitrile, the yield is 85% .

[0043]2.2 Preparation of 2-amino-3-methylbutanamide:

[0044] In a 1000ml flask, add 14 grams of sodium hydroxide, 500ml of methanol, and 50 grams of distilled water, stir to dissolve the solid, add 85g of 2-amino-3-methylbutyronitrile, cool to below 0°C, add 60 grams of acetone, and React at ~5°C for 5 hours, concentrate under reduced pressure at 38°C to recover the so...

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Abstract

The invention discloses a method for synthesizing D-valine, which comprises the following steps of: cyaniding isobutylaldehyde serving as an initiative raw material to prepare 2-amino-3-methyl-butanenitrile; performing catalytic hydrolysis by adopting inorganic base and a ketone catalyst to obtain mix spin freebase(+ / -)-2-amino-3-methylbutyrylamide; resolving by using a resolving agent of dibenzoyl-L-tartaric acid (L-DBTA) in a mixed solvent of acetone and water to obtain D-2-amino-3-methylbutyrylamideL-DBTA salt solid with optical activity; and acidifying and separating the resolving agent, and performing reflux hydrolysis and refining to obtain D-2-amino-3-methyl-butanoic acid, namely D-valine. The method has the advantages that: raw materials are low in cost and easily obtained, the method is easy and convenient to operate, the cost is low, the environmental pollution is light, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the preparation of pharmaceutical intermediates, in particular to a synthesis method of chiral amino acid D-valine. Background technique [0002] D-valine, also known as D-2-amino-3-methylbutyric acid, is an important chiral compound, which is widely used as a chemical intermediate in the synthesis of drugs and agricultural pesticides, such as anticancer Drug diaryl boronic acid, synthesis of new insecticide pyrethroids, etc. Because diiodophthaloyl in D-valine has antibacterial activity, its penicillamine derivative is an effective AIDS treatment drug. [0003] In addition, D-valine is an important organic chiral source, which is mainly used in the fields of chiral drugs, chiral additives and chiral auxiliary agents. At present, it is mainly used for the production of new broad-spectrum antibiotics, D-valinol and peptide synthesis, and plays an irreplaceable important role in the asymmetric synthesis of certain chiral compou...

Claims

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Application Information

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IPC IPC(8): C07C229/08C07C227/34
Inventor 阙利民吴争光蔡彤
Owner ABA CHEM SHANGHAI
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