Method for resolving 3-chloro-phenylglycine enantiomers through liquid-liquid extraction

A technology for phenylglycine and enantiomers, which is applied in the field of liquid-liquid extraction and separation of 3-chloro-phenylglycine enantiomers, can solve the problems of low extraction efficiency, low distribution coefficient and the like, and achieves high extraction efficiency, high separation factor, Simple and convenient operation

Active Publication Date: 2020-05-15
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the above-mentioned liquid-liquid extraction resolution method has a higher separation factor, there is a problem that the distribution coefficient (k) is low during the extraction process, so the extraction efficiency is low

Method used

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  • Method for resolving 3-chloro-phenylglycine enantiomers through liquid-liquid extraction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Add 0.1mmol (S,S)-(-)-2,2'-bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1'- Dissolve bis(diphenylphosphino)ferrocene and 0.1mmol bis(acetonitrile)dichloropalladium in 100mL 1,2-dichloroethane, stir for 16 hours to form a chiral extraction with a concentration of 1.0mmol / L agent;

[0025] (2) Dissolve 0.2 mmol of 3-chloro-phenylglycine enantiomer in 100 mL of sodium dihydrogen phosphate / disodium hydrogen phosphate buffered aqueous solution with a pH value of 7.0 to obtain 2.0 mmol / L of 3-chloro-benzene Glycine enantiomer aqueous phase;

[0026] (3) Mix 10mL of the organic phase and the aqueous phase in step (1) and step (2), shake in a water bath constant temperature oscillator at 5°C for 24 hours, then let stand for 48 hours to separate the two phases, and apply high-efficiency liquid Determination of partition coefficient k of D-3-chloro-phenylglycine and L-3-chloro-phenylglycine and 3-chloro-phenylglycine in organic phase and aqueous phase respectively by phase ...

Embodiment 2

[0028] (1) Add 0.3mmol (S,S)-(-)-2,2'-bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1'- Bis(diphenylphosphino)ferrocene and 0.3mmol bis(acetonitrile)dichloropalladium were dissolved in 100mL of dichloromethane, stirred for 16 hours to form a chiral extractant with a concentration of 3.0mmol / L;

[0029] (2) Dissolve 0.2 mmol of 3-chloro-phenylglycine enantiomer in 100 mL of sodium dihydrogen phosphate / disodium hydrogen phosphate buffered aqueous solution with a pH value of 7.0 to obtain 2.0 mmol / L of 3-chloro-benzene Glycine enantiomer aqueous phase;

[0030] (3) Mix 10mL of the organic phase and the aqueous phase in step (1) and step (2), shake in a water bath constant temperature oscillator at 5°C for 24 hours, then let stand for 48 hours to separate the two phases, and apply high-efficiency liquid Determination of partition coefficient k of D-3-chloro-phenylglycine and L-3-chloro-phenylglycine and 3-chloro-phenylglycine in organic phase and aqueous phase respectively by phas...

Embodiment 3

[0032] (1) Add 0.1mmol (S,S)-(-)-2,2'-bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1'- Dissolve bis(diphenylphosphino)ferrocene and 0.1mmol palladium acetate in 100mL dichloromethane, stir for 17 hours to form a chiral extractant with a concentration of 1.0mmol / L;

[0033] (2) Dissolve 0.2 mmol of 3-chloro-phenylglycine enantiomer in 100 mL of sodium dihydrogen phosphate / disodium hydrogen phosphate buffered aqueous solution with a pH value of 7.0 to obtain 2.0 mmol / L of 3-chloro-benzene Glycine enantiomer aqueous phase;

[0034] (3) Mix 10mL of the organic phase and the aqueous phase in step (1) and step (2), shake in a water bath constant temperature oscillator at 10°C for 24 hours, then let stand for 48 hours to separate the two phases, and apply high-efficiency liquid Determination of partition coefficient k of D-3-chloro-phenylglycine and L-3-chloro-phenylglycine and 3-chloro-phenylglycine in organic phase and aqueous phase respectively by phase chromatography D and k L...

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Abstract

The invention relates to the technical field of medicinal chemistry, and in particular, relates to a method for resolving 3-chloro-phenylglycine enantiomers through liquid-liquid extraction. The method comprises the steps: dissolving a chiral ferrocene diphosphine ligand and palladium ions in an organic solvent to obtain an organic phase containing a chiral extractant; dissolving a 3-chloro-phenylglycine enantiomer in a buffer aqueous solution with a pH value of 7-9 to obtain an aqueous phase containing the 3-chloro-phenylglycine enantiomer; mixing the organic phase containing the chiral extractant and the aqueous phase containing the 3-chloro-phenylglycine enantiomer, oscillating, standing until the organic phase and the aqueous phase are separated, and respectively enriching the two enantiomers of 3-chloro-phenylglycine in the organic phase and the aqueous phase to realize separation. Compared with the prior art, the method has the advantages of being high in extraction efficiency, simple in process, low in cost and easy to industrialize.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a method for liquid-liquid extraction and resolution of 3-chloro-phenylglycine enantiomers. Background technique [0002] 3-Chloro-phenylglycine is an α-amino acid and is an important intermediate of pyrrole and imidazole pesticides. In addition, it can also be used to synthesize penicillin derivatives and cephalosporin derivatives. 3-Chloro-phenylglycine is a chiral molecule. In the prior art, the preparation methods of single enantiomer mainly include asymmetric synthesis method and racemate crystallization resolution method. [0003] Such as: literature (Yang Guang. Synthesis of photoactive α-amino acids by asymmetric phase transfer catalysis[J]. Chemical Reagents, 2002,24(2):136-138.) using two different chiral phase transfer catalysts (N- Benzyl cinchonidine chloride, N-benzyl cinchonine chloride) synthesized the corresponding R-type and S-type α-chlorophenylgly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/34C07C229/36
CPCC07C227/34C07B2200/07C07C229/36Y02P20/584
Inventor 刘雄陈树欢马雨肖文洁
Owner HUNAN UNIV OF SCI & TECH
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