m-Chloroperbenzoic acid → HCID 70400293, compound

HRID 371061Notes

Reaction equation

HRID 371061 reaction equation
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[S:21][CH3:22])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:24])[CH:4]=[CH:5][C:6](=[O:23])[CH:7]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[S:21]([CH3:22])=[O:33])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:24])[CH:4]=[CH:5][C:6](=[O:23])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70400268HCID 70400268, compound

Product 1

HCID 70400293HCID 70400293, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of (11β,17β)-9-fluoro-11-hydroxy-17-(methylthio)androsta-1,4-dien-3-one (701 mg, 2.0 mmole; see example 5) in chloroform (30 ml) was added a solution of 85% m-chloroperbenzoic acid (398 mg, 2.0 mmole) in chloroform (10 ml). An instantaneous reaction was observed (tlc). The solution was then washed with a 10% potassium carbonate solution and water, dried (anhydrous magnesium sulfate) and evaporated to afford the title compound as a solid (700 mg). One crystallization of this from acetone-hexane followed by drying (100° C., 0.3 mm of Hg, 10 hours) gave the analytical specimen of the title compound (600 mg) melting point 270°-272° C. dec., as a mixture of sulfoxide stereoisomers, with consistent spectral data.

Workup

  1. customAn instantaneous reaction
  2. washThe solution was then washed with a 10% potassium carbonate solution and water
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-37ae8039030f4a938e3d77576931f7c5
Source dataset
uspto-grants-1985_07
Patent number
US04529548

Reaction notes

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