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

HRID 327772
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HRID 327772 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 10219390chromium (VI) trioxide촉매HCID 176Acetic Acid용매2회
HCID 962
Water
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-146a4bc958f94495b7633bbfbadc136e
출처 데이터셋
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05274088

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