HRID538966

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID180

Acetone

C3H6O

结构：C=C(C)[C@@H]1CC[C@]2(CO)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

HCID72326

(+)-Betulin

C30H50O2

PRODUCTS

生成物

结构：C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

HCID122844

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

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 %).

WORKUP

后处理

customto obtain
customan organic synthesis reaction product
filtrationfiltering
concentrationconcentrating
customthe obtained reaction product
custominto the concentrated reaction product to liquid-liquid
extractionextract betulonic acid
additionc) introducing a saturated aqueous sodium chloride solution (brine) into the ethyl acetate solution
dissolutionin which the extracted betulonic acid is dissolved
washto wash the ethyl acetate solution
customremove impurities
additiond) introducing hexane or petroleum ether
customas a nonpolar solvent, into the ethyl acetate solution to remove nonpolar substances
additionfilled with aluminum oxide or silica gel, as a polar adsorbent
customto remove polar substances
dry with materialdrying the ethyl acetate solution

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d55b25ee02a246768e2f0abd9053b126
来源数据集: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08865935B2
来源说明: uspto-grants-2014_10

反应 SMILES

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]