Acetone → (+)-Betulonic acid

HRID 538966ノート

反応式

HRID 538966 の反応式
CC(C)=[O:3].[CH3:5][C:6]([C@H:8]1[C@@H:12]2[C@@H:13]3[C@@:26]([CH3:29])([CH2:27][CH2:28][C@@:11]2([CH2:35][OH:36])[CH2:10][CH2:9]1)[C@@:25]1([CH3:30])[C@@H:16]([C@:17]2([CH3:34])[C@@H:22]([CH2:23][CH2:24]1)[C:21]([CH3:32])([CH3:31])[C@@H:20]([OH:33])[CH2:19][CH2:18]2)[CH2:15][CH2:14]3)=[CH2:7]>C(OCC)(=O)C>[CH3:7][C:6]([C@H:8]1[C@@H:12]2[C@@H:13]3[C@@:26]([CH3:29])([CH2:27][CH2:28][C@@:11]2([C:35]([OH:3])=[O:36])[CH2:10][CH2:9]1)[C@@:25]1([CH3:30])[C@@H:16]([C@:17]2([CH3:34])[C@@H:22]([CH2:23][CH2:24]1)[C:21]([CH3:32])([CH3:31])[C:20](=[O:33])[CH2:19][CH2:18]2)[CH2:15][CH2:14]3)=[CH2:5]

参加物

4

反応物 2

HCID 180AcetoneHCID 72326Betulin

生成物 1

HCID 122844(+)-Betulonic acid

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

In order to accomplish the above objects, an aspect of the present invention provides a method of purifying betulonic acid, including the steps of: a) injecting a Jones oxidation reagent (CrO3/c-H2SO4/H2O) into a mixed solution of acetone and betulin to obtain an organic synthesis reaction product and filtering and concentrating the obtained reaction product; b) introducing ethyl acetate into the concentrated reaction product to liquid-liquid extract betulonic acid; c) introducing a saturated aqueous sodium chloride solution (brine) into the ethyl acetate solution, in which the extracted betulonic acid is dissolved, to wash the ethyl acetate solution and remove impurities therefrom; d) introducing hexane or petroleum ether, as a nonpolar solvent, into the ethyl acetate solution to remove nonpolar substances, passing the washed ethyl acetate solution through an adsorption tower filled with aluminum oxide or silica gel, as a polar adsorbent, to remove polar substances, and then drying the ethyl acetate solution to produce betulonic acid (purity: more than 92%, yield to birch bark: 2.75 wt %); and e) dissolving the produced betulonic acid in a mixed solvent of ethanol and acetonitrile, separating and treating the mixed solution using a semi-preparative chromatography column filled with C18 stationary phase, and then drying the separated and treated mixed solution to produce high-purity betulonic acid (purity: more than 99.5%, yield to birch bark: 1.8 wt %).

後処理

  1. customto obtain
  2. customan organic synthesis reaction product
  3. filtrationfiltering
  4. concentrationconcentrating
  5. customthe obtained reaction product
  6. custominto the concentrated reaction product to liquid-liquid
  7. extractionextract betulonic acid
  8. additionc) introducing a saturated aqueous sodium chloride solution (brine) into the ethyl acetate solution
  9. dissolutionin which the extracted betulonic acid is dissolved
  10. washto wash the ethyl acetate solution
  11. customremove impurities
  12. additiond) introducing hexane or petroleum ether
  13. customas a nonpolar solvent, into the ethyl acetate solution to remove nonpolar substances
  14. additionfilled with aluminum oxide or silica gel, as a polar adsorbent
  15. customto remove polar substances
  16. dry with materialdrying the ethyl acetate solution

出典と根拠

ORDレコード
ord-d55b25ee02a246768e2f0abd9053b126
出典データセット
uspto-grants-2014_10
特許番号
US08865935B2

反応ノート

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