m-Chloroperbenzoic acid → (11beta)-16-Chloro-17-(ethylsulfinyl)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-one

HRID 2286325Notes

Reaction equation

HRID 2286325 reaction equation
[Cl:1][C:2]1[CH2:7][C@H:6]2[C@H:8]3[C@:18]([F:22])([C@@H:19]([OH:21])[CH2:20][C@:4]2([CH3:5])[C:3]=1[S:24][CH2:25][CH3:26])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]1)[CH2:10][CH2:9]3.ClC1C=CC=C(C(OO)=[O:35])C=1>ClCCl>[Cl:1][C:2]1[CH2:7][C@H:6]2[C@H:8]3[C@:18]([F:22])([C@@H:19]([OH:21])[CH2:20][C@:4]2([CH3:5])[C:3]=1[S:24]([CH2:25][CH3:26])=[O:35])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]1)[CH2:10][CH2:9]3

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70562795(11beta)-16-Chloro-17-(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-one

Product 1

HCID 70563103(11beta)-16-Chloro-17-(ethylsulfinyl)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To (11β)-16-chloro-17-(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-one (100 mg; see Example 1A) in dichloromethane (15 ml) is added a solution of 85% m-chloroperbenzoic acid (56 mg) in dichloromethane (5.0 ml) over a period of 2 minutes. After 1 hour the solution is washed with a dilute sodium carbonate solution and water, dried (anhydrous MgSO4) and evaporated to yield the title compound.

Workup

  1. washAfter 1 hour the solution is washed with a dilute sodium carbonate solution and water
  2. dry with materialdried (anhydrous MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-4c37446d4a2840e0a1aff28a893156ba
Source dataset
uspto-grants-1981_05
Patent number
US04265815

Reaction notes

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