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Method for splitting halogenated alpha-amino acid

A technology of amino acid and halogenation, which is applied in the field of production process of halogenated α-amino acid, to achieve the effect of simple operation, mild reaction conditions and high product purity

Inactive Publication Date: 2013-05-01
ZHANGJIAGANG JIUMU TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Halogenated α-amino acids with a single configuration play an important role in drug synthesis, and these optically active halogenated α-amino acids are required to be industrially produced, and require stable, environmentally friendly, safe, low-cost, and mild reaction conditions. method and process, the current literature methods are difficult to achieve such a goal

Method used

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  • Method for splitting halogenated alpha-amino acid
  • Method for splitting halogenated alpha-amino acid
  • Method for splitting halogenated alpha-amino acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment one: the separation process of L-chloroalanine and D-chloroalanine

[0026] 1. Synthesis of N-phenylacetyl-DL-chloroalanine:

[0027] Add 123.5gDL-chloroalanine, 40gNaOH, and 500ml water into a 1000ml reaction flask, stir fully at 0°C, add 170g of phenylacetyl chloride dropwise under stirring, control pH=8-10 during the reaction, and temperature 0°C Next, after the completion of the dropwise addition, keep the reaction for 2 hours, then continue to stir the reaction at room temperature for 3 hours, stop the reaction, add concentrated hydrochloric acid to adjust the pH to 1-2, a large amount of white solid is precipitated, vacuum filtration to obtain 229.5g of white solid N -Phenylacetyl-DL-chloroalanine. The properties of the products obtained were determined by HPLC (High Performance Liquid Chromatography).

[0028] 2. Enzymatic hydrolysis of N-phenylacetyl-DL-chloroalanine:

[0029] Add 120.5g of N-phenylacetyl-DL-chloroalanine solid obtained in the prev...

Embodiment 2

[0035] Embodiment two: the separation process of L-bromoalanine and D-bromoalanine

[0036] 1. Synthesis of N-phenylacetyl-DL-bromoalanine:

[0037] Add 168gDL-bromoalanine, 40gNaOH, and 600ml water into a 1000ml reaction flask, stir fully at -5°C, add 170g of phenylacetyl chloride dropwise under stirring, control pH=8-9 during the reaction, and temperature -5 Below ℃, keep the reaction for 4 hours after the dropwise addition is completed, then continue to stir the reaction at room temperature for 5 hours, stop the reaction, add dilute sulfuric acid to adjust the pH to 1-2, a large amount of solids are precipitated, vacuum filtration, and 266g of white solid N- Phenylacetyl-DL-bromoalanine.

[0038] The properties of the products obtained were determined by HPLC (High Performance Liquid Chromatography).

[0039] 2. Enzymatic hydrolysis of N-phenylacetyl-DL-bromoalanine:

[0040] Add 143g of N-phenylacetyl-DL-bromoalanine solid obtained in the previous step into a 2000ml react...

Embodiment 3

[0045] Example 3: Resolution process of L-fluoroalanine and D-fluoroalanine

[0046] 1. Synthesis of N-phenylacetyl-DL-fluoroalanine:

[0047] Add 107.1gDL-fluoroalanine, 40gNaOH, and 450ml water into a 1000ml reaction flask, stir well at -2°C, add 170g of phenylacetyl chloride dropwise under stirring, control pH=8-9 during the reaction, temperature- Below 2°C, keep warm for 3 hours after the dropwise addition, then continue to stir and react at room temperature for 2 hours, stop the reaction, add concentrated hydrochloric acid to adjust the pH to 1-2, a large amount of white solid precipitates, and vacuum filter to obtain 209.5g of white Solid N-phenylacetyl-DL-fluoroalanine.

[0048] The properties of the products obtained were determined by HPLC (High Performance Liquid Chromatography).

[0049] 2. Enzymatic hydrolysis of N-phenylacetyl-DL-fluoroalanine:

[0050] Add 112.6g of N-phenylacetyl-DL-fluoroalanine solid obtained in the previous step into a 2000ml reaction flas...

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Abstract

The invention relates to a method for splitting halogenated alpha-amino acid. According to the invention, after N-acylation of halogenated alpha-amino acid, an acyl group of N-acylated alpha-amino acid with one structure is highly selectively hydrolyzed through selection of a proper enzyme, while a counterpart of the N-acylated alpha-amino acid with the structure does not undergo hydrolysis of acyl group; then separation is carried out based on difference between halogenated alpha-amino acid and N-acyl halogenated alpha-amino acid to obtain optically pure halogenated alpha-amino acid; and optically pure N-acyl halogenated alpha-amino acid undergoes chemical hydrolysis so as to obtain corresponding optically pure halogenated alpha-amino acid. The method provided by the invention has the advantages of stability, environment-friendliness, safety, mild production conditions, capacity of obtaining a product with optical purity as high as 99.9% and low production cost. The method provides a novel approach for industrial production of halogenated alpha-amino acid with high optical purity.

Description

technical field [0001] The invention relates to a production process of halogenated α-amino acid with high optical purity. Specifically, the present invention relates to a process for obtaining the corresponding optically pure halogenated α-amino acid by using penicillin acylase to catalyze the hydrolysis of racemic halogenated α-amino acid derivatives for enantiomer resolution. Background technique [0002] Halogenated α-amino acids are organic acids containing amino groups, most of which have two mirror-image enantiomers L-halogenated α-amino acids and D-halogenated α-amino acids. Optically active L-halogenated α-amino acids and D-halogenated α-amino acids have physiological activity and are synthetic intermediates of chiral medicines, pesticides or other chiral fine chemical products. One or the other photoactive enantiomer is obtained. [0003] L-chloroalanine is a kind of L-halogenated α-amino acid, which is a physiologically active amino acid, through which L-serine,...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P13/04
Inventor 敬炳文李翠容赵正达
Owner ZHANGJIAGANG JIUMU TECH
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