m-Chloroperbenzoic acid → (11beta,17beta)-17-(Ethylsulfinyl)-9-fluoro-11-hydroxyandrosta-1,4-dien-3-one

HRID 371062Notes

Reaction equation

HRID 371062 reaction equation
[CH2:1]([S:3][C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@:20]([F:24])([C@@H:21]([OH:23])[CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH:16]=[CH:17]1)[CH2:12][CH2:11]3)[CH3:2].ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)(Cl)Cl>[CH2:1]([S:3]([C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@:20]([F:24])([C@@H:21]([OH:23])[CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH:16]=[CH:17]1)[CH2:12][CH2:11]3)=[O:34])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70401069(11beta,17beta)-17-(Ethylthio)-9-fluoro-11-hydroxyandrosta-1,4-dien-3-one

Product 1

HCID 70401104(11beta,17beta)-17-(Ethylsulfinyl)-9-fluoro-11-hydroxyandrosta-1,4-dien-3-oneYield 95.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of (11β,17β)-17-(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4-dien-3-one (700 mg, 1.92 mmole; see example 6) in chloroform (30 ml) was added a solution of 86% m-chloroperbenzoic acid (390 mg, 1.95 mmole) in chloroform (15 ml). An instantaneous reaction was noted (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 (697 mg) as a solid. One crystallization of this from ethyl acetate followed by drying (100° C., 0.3 mm of Hg, 10 hours) gave the analytical specimen of the title compound (600 mg), melting point 247°-250° C., 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-37be5d94938947bda3f2dd8977eee14b
Source dataset
uspto-grants-1985_07
Patent number
US04529548

Reaction notes

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