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Potassium Iodide → (2beta,3alpha,5alpha)-21-(Acetyloxy)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione

HRID 233496
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Reaktionsgleichung

Reaktionsgleichung von HRID 233496
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].Cl[CH2:7][C:8](=[O:38])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C:24](=[O:28])[CH2:25]2)[C@:21]2([CH3:22])[C@H:16]([CH2:17][C@H:18]([OH:37])[C@@H:19]([N:29]4[CH2:34][CH2:33][O:32][C:31]([CH3:36])([CH3:35])[CH2:30]4)[CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1.[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>O.CN(C)C=O.C(O)(=O)C>[C:1]([O:4][CH2:7][C:8](=[O:38])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C:24](=[O:28])[CH2:25]2)[C@:21]2([CH3:22])[C@H:16]([CH2:17][C@H:18]([OH:37])[C@@H:19]([N:29]4[CH2:34][CH2:33][O:32][C:31]([CH3:36])([CH3:35])[CH2:30]4)[CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 10672358(2beta,3alpha,5alpha)-21-Chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione

Produkt 1

HCID 10529493(2beta,3alpha,5alpha)-21-(Acetyloxy)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione
Ausbeute 62,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Potassium acetate (0.83 g) was added to a solution of the 21-chloro compound of Example 2 (0.5 g), potassium iodide (0.04 g), glacial acetic acid (1.05 ml) and N,N-dimethylformamide (20 ml) and the mixture was heated at 65° C. in an atmosphere of nitrogen for 1.5 h. The mixture was then poured into water (200 ml) and aqueous sodium carbonate was added until the pH exceeded 9. The precipitated solid was filtered off, washed with water and dissolved in dichloromethane. After drying over sodium sulfate, the solvent was removed under reduced pressure and the residue was crystallised from methanol to give (2β,3α,5α)-21-(acetyloxy)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (0.33 g). m.p. 158°-160° C.; [α]D +123° (c 0.68).

Aufarbeitung

  1. additionwas added until the pH
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with water
  4. dissolutiondissolved in dichloromethane
  5. dry with materialAfter drying over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was crystallised from methanol

Quellen und Nachweise

ORD-Eintrag
ord-7e8ebb7339a646dbbe9cef3a301ba951
Quelldatensatz
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05593983

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