Chiral resolution method of racemic alpha-cyclopentyl mandelic acid

Chiral resolution method of racemic alpha-cyclopentyl mandelic acid

  • CN 103,694,110 A
  • Filed: 12/12/2013
  • Published: 04/02/2014
  • Est. Priority Date: 12/12/2013
  • Status: Active Application
First Claim
Patent Images

1. a chiral separation method for racemic '"'"' alpha '"'"'-cyclopentyl amygdalic acid, is characterized in that described method carries out as follows:

  • (1) organic solvent A, organic solvent B and the phosphate buffered saline buffer that contains hydroxypropyl-beta-cyclodextrin are formed to solvent system according to volume ratio 1~

    9;

    1~

    9;

    10, mix, stratification, separatory obtains organic phase and water;

    The substitution value of described hydroxypropyl-beta-cyclodextrin is 4.5~

    8.0;

    The pH value of the described phosphate buffered saline buffer that contains hydroxypropyl-beta-cyclodextrin is 2.0~

    8.0;

    In the described phosphate buffered saline buffer that contains hydroxypropyl-beta-cyclodextrin, the concentration of hydroxypropyl-beta-cyclodextrin is 0.02~

    0.40mol/L;

    Described organic solvent A is the alkane of C1~

    C8;

    Described organic solvent B is the ester class of ether or the C3~

    C8 of C2~

    C8;

    (2) organic phase of racemic '"'"' alpha '"'"'-cyclopentyl step (1) gained for amygdalic acid is dissolved, make sample;

    (3) adopt high-speed countercurrent chromatography resolution of racemic α

    -cyclopentyl amygdalic acid;

    the organic phase that the step (1) of take obtains is stationary phase, water is moving phase, countercurrent chromatography separation column is filled up to stationary phase, column temperature is 2~

    35 ℃

    , opening speed controller, rotating speed is 200~

    2000rpm, flow velocity with 0.1~

    3.0mL/min pumps into moving phase in post, after two phase solvent system reaches fluid dynamic equilibrium, when moving phase flows out from chromatographic column exit, the sample that step (2) is made is by sampling valve sample introduction, UV-detector detects effluent liquid under wavelength 190~

    400nm, according to time gradient, with auto partial sampler, collect respectively the elutriant of 30min to the gradient timed interval between 200min, and according to the time period of the bimodal appearance of enantiomorph in ultraviolet detection spectrogram, the elutriant that leading peak was collected in the corresponding time period merges and obtains the leading peak elutriant containing target components dextrorotation α

    -cyclopentyl amygdalic acid monomer, the elutriant that postpeak was collected in the corresponding time period merges and obtains the postpeak elutriant containing the left-handed α

    -cyclopentyl of target components amygdalic acid monomer, described leading peak refers to the bimodal middle elder generation of enantiomorph main peak out, described postpeak refer to enantiomorph bimodal in after main peak out,(4) from step (3), collect in the leading peak elutriant obtaining and reclaim, obtain dextrorotation α

    -cyclopentyl amygdalic acid monomer;

    From step (3), collect in the postpeak elutriant obtaining and reclaim, obtain left-handed α

    -cyclopentyl amygdalic acid monomer.

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