Water → 3alpha,21-Di-azido-5alpha-pregnan-20-one

HRID 1829638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1829638
[N:1]([C@@H:4]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:14](=[O:17])[CH2:15]Br)[CH2:5]1)=[N+:2]=[N-:3].[N-:27]=[N+:28]=[N-:29].[Na+].O.C(OCC)(=O)C>CS(C)=O.[Cl-].[Na+].O>[N:1]([C@@H:4]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:14](=[O:17])[CH2:15][N:27]=[N+:28]=[N-:29])[CH2:5]1)=[N+:2]=[N-:3]

Komponenten

7

Edukt 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 866001863alpha-Azido-21-bromo-5alpha-pregnan-20-one

Produkt 1

HCID 102713733alpha,21-Di-azido-5alpha-pregnan-20-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A solution of 3α-azido-21-bromo-5α-pregnan-20-one (35 mg, 0.083 mmol) in DMSO (3 mL) was treated with sodium azide (33 mg, 0.5 mmol) and the resulting mixture was stirred at RT for 24 h. Addition of water and ethyl acetate and extraction of the organic layer with water, brine, drying (Na2SO4) and evaporation of the solvent in vacuo afforded after purification of the residue using flash colunm chromatography with dichloromethane/ethyl acetate 90/10 as elution solvent the compound named above.

Aufarbeitung

  1. customdrying
  2. custom(Na2SO4) and evaporation of the solvent in vacuo
  3. customafforded
  4. customafter purification of the residue
  5. washas elution solvent the compound

Quellen und Nachweise

ORD-Eintrag
ord-fb5a6fa2050f41b7bf7ccb349f60d87c
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064116B2

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