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

HRID 1829638Notes

Reaction equation

HRID 1829638 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fb5a6fa2050f41b7bf7ccb349f60d87c
Source dataset
uspto-grants-2006_06
Patent number
US07064116B2

Reaction notes

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