Sodium Azide → HCID 57545168, compound

HRID 1661526Notes

Reaction equation

HRID 1661526 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][CH2:7][O:8][C:9]1[CH:35]=[CH:34][C:12]2[C@:13]3([OH:33])[C@@H:18]([OH:19])[CH2:17][C@@H:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C@:14]3([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[O:15][C:11]=2[CH:10]=1>CN(C=O)C>[N:1]([CH2:6][CH2:7][O:8][C:9]1[CH:35]=[CH:34][C:12]2[C@:13]3([OH:33])[C@@H:18]([OH:19])[CH2:17][C@@H:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C@:14]3([C:26]3[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=3)[O:15][C:11]=2[CH:10]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57545193HCID 57545193, compound

Product 1

HCID 57545168HCID 57545168, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

56.9 mg (0.87 mmol) of sodium azide are added to 200 mg (0.44 mmol) of (1S*,3S*,3aR*,8bS*)-6-(2-chloroethoxy)-3a-(4-chlorophenyl)-3-phenyl-2,3,3a,8b-tetrahydrocyclopenta[b]benzofuran-1,8b-(1H)-diol (Example 48A) in 4 ml of DMF under argon, and the mixture is heated at 100° C. overnight. After cooling and concentration, the residue is taken up in water and dichloromethane, the phases are separated, the aqueous phase is extracted twice with dichloromethane, and the combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. Gradient chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate) results in 190 mg (94% of theory) of the product.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentration
  3. customdichloromethane, the phases are separated
  4. extractionthe aqueous phase is extracted twice with dichloromethane
  5. washthe combined organic phases are washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customGradient chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate) results in 190 mg (94% of theory) of the product

Sources & evidence

ORD record
ord-668baa61c59f4185a0d056fd71550ed3
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

Loading…