Hydrogen Peroxide → (+)-Betulonic acid

HRID 414904ノート

反応式

HRID 414904 の反応式
[CH3:1][C:2]([C@H:4]1[C@@H:8]2[C@H:9]3[C@@:14]([CH3:17])([CH2:15][CH2:16][C@@:7]2([CH:31]=[O:32])[CH2:6][CH2:5]1)[C@:13]1([CH3:30])[CH2:18][CH2:19][C@H:20]2[C:26]([CH3:28])([CH3:27])[C:24](=[O:25])[CH:23]=[CH:22][C@:21]2([CH3:29])[C@H:12]1[CH2:11][CH2:10]3)=[CH2:3].OO.[O-:35]Cl=O.[Na+]>CC#N.O.O>[CH3:3][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:14]([CH3:17])([CH2:15][CH2:16][C@@:7]2([C:31]([OH:35])=[O:32])[CH2:6][CH2:5]1)[C@@:13]1([CH3:30])[C@@H:12]([C@:21]2([CH3:29])[C@@H:20]([CH2:19][CH2:18]1)[C:26]([CH3:28])([CH3:27])[C:24](=[O:25])[CH2:23][CH2:22]2)[CH2:11][CH2:10]3)=[CH2:1]

参加物

6

反応物 3

HCID 784Hydrogen PeroxideHCID 23668197Sodium ChloriteHCID 44559212Betulone Aldehyde

生成物 1

HCID 122844(+)-Betulonic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 18373917Acetonitrile--water (1/1)溶媒

反応条件

温度
2.5 °C

実験手順

The betulone aldehyde prepared from the last step is dissolved in a mixture of NaH2PO4.H2O (877 mg) and CH3CN—H2O (17 mL) and the suspension cooled to 0-5° C. 30% aqueous H2O2 (220 μL) and a solution of NaClO2 (200 mg) in water (16 mL) are then successively added, the mixture warmed to room temperature and stirred at this temperature for 1 h. The reaction is quenched by addition of Na2S2O5 (380 mg), and extracted with ethyl acetate. The organic extract is washed with water and brine, dried (Na2SO4), filtered, and concentrated. The residue is then subjected to column chromatography to afford betulonic acid (550 mg) as white solid.

後処理

  1. temperaturethe mixture warmed to room temperature
  2. customThe reaction is quenched by addition of Na2S2O5 (380 mg)
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washis washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-ae05c6e12d1f40a1be49aa744b0431b9
出典データセット
uspto-grants-2012_01
特許番号
US08088757B2

反応ノート

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