Acetic Anhydride → HCID 15586530, Verbindung

HRID 614998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 614998
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH:14]=[C:15]3[S:21]([CH3:23])=O)[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:25])[CH:4]=[CH:5][C:6](=[O:24])[CH:7]=1.[C:26]([O:29]C(=O)C)(=[O:28])[CH3:27]>>[C:26]([O:29][CH2:23][S:21][C:15]1[C@:16]2([CH2:18][C@H:19]([OH:20])[C@@:2]3([F:1])[C@@H:11]([CH2:10][CH2:9][C:8]4[C@:3]3([CH3:25])[CH:4]=[CH:5][C:6](=[O:24])[CH:7]=4)[C@@H:12]2[CH2:13][CH:14]=1)[CH3:17])(=[O:28])[CH3:27]

Komponenten

3

Edukt 2

HCID 7918Acetic AnhydrideHCID 14823693HCID 14823693, Verbindung

Produkt 1

HCID 15586530HCID 15586530, Verbindung

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 1.5 g of 9-fluoro-11β-hydroxy-17-(methylsulfinyl)androsta-1,4,16-trien -3-one, 70 ml of acetic anhydride and 2 g of fused sodium acetate is heated at 110° C. under nitrogen for 2 hours. The acetic anhydride is partially removed by distillation under vacuum and the resulting slurry is diluted with 1:1 chloroform-water. The organic layer is separated, washed with diluted sodium bicarbonate solution, water, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue is dissolved in 4:1 chloroform-hexane and chromatographed on a 40 g-silica gel column. Elution with 1:4 hexane-chloroform gives 940 mg of slightly impure material. Two crystallizations from acetone-hexane give 350 mg of the title compound, melting point 193°-194° C., with consistent spectral data.

Aufarbeitung

  1. customThe acetic anhydride is partially removed by distillation under vacuum
  2. additionthe resulting slurry is diluted with 1:1 chloroform-water
  3. customThe organic layer is separated
  4. washwashed with diluted sodium bicarbonate solution, water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. dissolutionThe residue is dissolved in 4:1 chloroform-hexane
  8. customchromatographed on a 40 g-silica gel column
  9. washElution with 1:4 hexane-chloroform
  10. customgives 940 mg of slightly impure material
  11. customTwo crystallizations from acetone-hexane

Quellen und Nachweise

ORD-Eintrag
ord-1e7b2cce9feb448595080ac1588ab066
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04146538

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