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Sodium Iodide → 21-Iodo-20-methyl-1alpha,3beta-bis(methoxycarbonyloxy)-pregna-5,7-diene

HRID 1587633
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1587633
[CH3:1][CH:2]([C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C@@H:24]([O:39][C:40]([O:42][CH3:43])=[O:41])[CH2:25][C@@H:26]2[O:34][C:35]([O:37][CH3:38])=[O:36])=[CH:21][CH:20]=3)[CH2:17][CH2:16]1)[CH2:3]OS(C1C=CC(C)=CC=1)(=O)=O.[I-:44].[Na+]>CC(C)=O>[I:44][CH2:3][CH:2]([CH3:1])[C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C@@H:24]([O:39][C:40]([O:42][CH3:43])=[O:41])[CH2:25][C@@H:26]2[O:34][C:35]([O:37][CH3:38])=[O:36])=[CH:21][CH:20]=3)[CH2:17][CH2:16]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 8674694320-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-p-toluenesulfonyloxypregna-5,7-diene

Produkt 1

HCID 6778826821-Iodo-20-methyl-1alpha,3beta-bis(methoxycarbonyloxy)-pregna-5,7-dieneAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 53 mg of 20-methyl-1α,3β-bis-(methoxycarbonyloxy)-21-p-toluenesulfonyloxypregna-5,7 -diene in 5 ml of acetone was added 120 mg of sodium iodide and the mixture was heated under reflux for 4 hours. The reaction mixture was cooled, then the acetone was distilled off under reduced pressure, water was added to the residue, and the resulting mixture was extracted with diethyl ether. The extract was washed with water, an aqueous solution of sodium thiosulfate, water, an aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium chloride, then dried over sodium sulfate and concentrated. Purification of the residue by silica gel column chromatography gave 38 mg of 21-iodo-20-methyl-1α,3β-bis(methoxycarbonyloxy)-pregna-5,7-diene.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. distillationthe acetone was distilled off under reduced pressure, water
  5. additionwas added to the residue
  6. extractionthe resulting mixture was extracted with diethyl ether
  7. washThe extract was washed with water
  8. dry with materialan aqueous solution of sodium thiosulfate, water, an aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium chloride, then dried over sodium sulfate
  9. concentrationconcentrated
  10. customPurification of the residue by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cd9e82362a1c422cb0615f4bd257cc6f
Quelldatensatz
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05218109

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