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New method for reactive extraction of 4-nitro-phenylglycine

A technology of phenylglycine and nitro group, which is applied in the field of chiral extraction and separation of amino acid racemates, can solve the problem of low enantioselectivity in separation of amino acids, and achieves good repeatability, high enantioselectivity, and easy industrial production. Effect

Inactive Publication Date: 2014-11-26
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This patent proposes a new chiral extraction method based on the problem of low selectivity of amino acid enantiomers in the extraction and separation of general chiral metal complexes: based on chiral BINAP (2,2'-bisdiphenylphosphino-1 ,1'-Binaphthyl)-metal complex chiral extraction technique

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Copper hexafluorophosphate tetraacetonitrile ( ) As the central ion donor of the extractant, it reacts with chiral (S)-BINAP in 1,2-dichloroethane to obtain (S)-BINAP-copper ( ) The solution of the complex, control the (S)-BINAP and copper ( ) The ion concentration is 1 mmol / L. D,L-4-nitro-phenylglycine dissolved in 0.1 mol / L NaH 2 PO 4 / Na 2 HPO 4 Adjust pH = 7.0 in the buffer solution and control the concentration of D,L-4-nitro-phenylglycine to 2 mmol / L. The organic phase and the water phase are obtained through the above two steps. Take 500 mL each of the organic phase and the water phase in an Erlenmeyer flask, shake in a constant temperature shaker in a water bath for 12 hours, control the constant temperature at 5°C, mix well and stand for stratification, so that the two phases reach equilibrium. Determine the concentration of 4-nitro-phenylglycine enantiomers in the organic phase and the aqueous phase, and perform constant calculation of materials to determine...

Embodiment 2

[0012] Copper hexafluorophosphate tetraacetonitrile ( ) As the central ion donor of the extractant, it reacts with chiral (S)-BINAP in 1,2-dichloroethane to obtain (S)-BINAP-copper ( ) The solution of the complex, controlling the (S)-BINAP and copper( ) The ion concentration ratio is 0.5, and the copper ion concentration is 2 mmol / L. D,L-4-nitro-phenylglycine dissolved in 0.1 mol / L NaH 2 PO 4 / Na 2 HPO 4 Adjust pH = 7.0 in the buffer solution and control the concentration of D,L-4-nitro-phenylglycine to 2 mmol / L. After the above two steps respectively

[0013] An organic phase and an aqueous phase are obtained. Take 2 mL each of the organic phase and the water phase in a test tube, shake in a constant temperature shaker in a water bath for 12 hours, control the constant temperature at 5°C, mix well and stand for stratification, so that the two phases reach equilibrium. Determine the concentration of 4-nitro-phenylglycine enantiomers in the organic phase and the aqueous phase,...

Embodiment 3

[0015] Copper hexafluorophosphate tetraacetonitrile ( ) As the central ion donor of the extractant, it reacts with chiral (S)-BINAP in 1,2-dichloroethane to obtain (S)-BINAP-copper ( ) The solution of the complex, controlling the (S)-BINAP and copper( ) The ion concentration ratio is 2, in which the copper ion concentration is 2 mmol / L. D,L-4-nitro-phenylglycine dissolved in 0.1 mol / L NaH 2 PO 4 / Na 2 HPO 4 Adjust pH = 7.0 in the buffer solution and control the concentration of D,L-4-nitro-phenylglycine to 2 mmol / L. The organic phase and the water phase are obtained through the above two steps. Take 2 mL each of the organic phase and the water phase in a test tube, shake in a constant temperature shaker in a water bath for 12 hours, control the constant temperature at 5°C, mix well and stand for stratification, so that the two phases reach equilibrium. Determine the concentration of 4-nitro-phenylglycine enantiomers in the organic phase and the aqueous phase, and perform con...

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Abstract

The invention relates to a new method for reactive extraction of a 4-nitro-phenylglycine enantiomer. A (S)-BINAP-metal copper complex is adopted as an organic phase chiral extractant for extraction separation of the 4-nitro-phenylglycine enantiomer dissolved in an aqueous phase. The invention also discloses a preparation method of the (S)-BINAP-metal copper complex. The (S)-BINAP-metal copper complex has good complexing ability and high stereoselectivity on the 4-nitro-phenylglycine enantiomer, and the separation factor (alpha) reaches over 4.1.

Description

technical field [0001] The invention relates to a method for chiral extraction and separation of amino acid racemates, which is characterized in that a metal complex is used as a chiral extraction agent to separate 4-nitro-phenylglycine enantiomers, specifically (S)-BINAP-copper The complex is used as a chiral extractant to extract and separate the enantiomers of 4-nitro-phenylglycine. Background technique [0002] α -Amino acid is a class of small molecular compounds that widely exist in nature. It has the function of preventing and curing diseases in medicine, especially the optically active amino acid has important biological activity and physiological function. An important precursor of a series of peptides. 4-Nitro-phenylglycine is an aromatic amino acid with physiological activity. As a derivative of phenylglycine, it is widely used in medicine and food industry. D,L-4-nitro-phenylglycine can be used as a D-type serine transporter inhibitor, and can be used clinica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/34C07C229/36
Inventor 唐课文张盼良刘昶周从山华杰阎建辉侯朝晖
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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