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Sodium Acetate → (25R)-16-oxo-26-phthalimidocholesterol

HRID 327772
ノート
印刷プレビュー

反応式

HRID 327772 の反応式
[OH:1][C@H:2]1[CH2:37][C@@H:36]2[C@:23]([CH3:40])([CH2:24][CH2:25][C@H:26]3[C@H:35]2[CH2:34][CH:33]=[C:32]2[C@:27]3([CH3:39])[CH2:28][CH2:29][C@H:30]([OH:38])[CH2:31]2)[C@H:3]1[C@H:4]([CH3:22])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:21])[CH2:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20].C([O-])(=O)C.[Na+]>O.C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[O:1]=[C:2]1[CH2:37][C@@H:36]2[C@:23]([CH3:40])([CH2:24][CH2:25][C@H:26]3[C@H:35]2[CH2:34][CH:33]=[C:32]2[C@:27]3([CH3:39])[CH2:28][CH2:29][C@H:30]([OH:38])[CH2:31]2)[C@H:3]1[C@H:4]([CH3:22])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:21])[CH2:9][N:10]1[C:11](=[O:20])[C:12]2=[CH:19][CH:18]=[CH:17][CH:16]=[C:13]2[C:14]1=[O:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 517045Sodium AcetateHCID 10962631(25R)-16beta-HYDROXY-26-PHTHALIMIDOCHOLESTEROL

生成物 1

HCID 9832896(25R)-16-oxo-26-phthalimidocholesterol収率 89%

試薬・触媒・溶媒 3

HCID 10219390chromium (VI) trioxide触媒HCID 176Acetic Acid溶媒2 回
HCID 962
Water
溶媒

実験手順

A solution of chromium trioxide (0.04 g, 0.4 mmoles) in water (0.15 ml) and acetic acid (0.3 ml) was added dropwise to a solution of (25R)-16β-hydroxy-26-phthalimidocholesterol (4) (0.26 g, 0.49 mmoles), and sodium acetate (1.00 g, 12.19 mmoles) in acetic acid (35 ml), and stirred for 18 hours at room temperature. The excess reagent was then destroyed with methanol (15 ml), and solvent was evaporated under reduced pressure. The resulting residue was diluted with water, and extracted with methylene chloride. The organic layer was washed with 5% K2CO3 and water, dried over sodium sulfate, and evaporated under reduced pressure to yield 0.23 g (89%) of (25R)-16-oxo-26-phthalimidocholesterol (5). The product was recrystallized from acetone and was found to have a melting point of 178°-180° C. Elemental and structural 1H-NMR) analyses of the product are described below.

後処理

  1. customThe excess reagent was then destroyed with methanol (15 ml), and solvent
  2. customwas evaporated under reduced pressure
  3. additionThe resulting residue was diluted with water
  4. extractionextracted with methylene chloride
  5. washThe organic layer was washed with 5% K2CO3 and water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-146a4bc958f94495b7633bbfbadc136e
出典データセット
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05274088

反応ノート

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