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

HRID 327772
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 327772
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10219390chromium (VI) trioxideKatalysatorHCID 176Acetic Acid
Lösungsmittel
2×
HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-146a4bc958f94495b7633bbfbadc136e
Quelldatensatz
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05274088

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