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Chlorosuccinimide → (11beta)-16-Chloro-17-(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-one

HRID 2286320
Notes
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Reaction equation

HRID 2286320 reaction equation
[CH2:1]([S:3][C:4]1[C@:5]2([CH2:22][C@H:21]([OH:23])[C@@:20]3([F:24])[C@@H:10]([CH2:11][CH2:12][C:13]4[C@:18]3([CH3:19])[CH:17]=[CH:16][C:15](=[O:25])[CH:14]=4)[C@@H:7]2[CH2:8][CH:9]=1)[CH3:6])[CH3:2].[Cl:26]N1C(=O)CCC1=O>ClCCl.C(Cl)(Cl)Cl>[Cl:26][C:9]1[CH2:8][C@H:7]2[C@H:10]3[C@:20]([F:24])([C@@H:21]([OH:23])[CH2:22][C@:5]2([CH3:6])[C:4]=1[S:3][CH2:1][CH3:2])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH:16]=[CH:17]1)[CH2:12][CH2:11]3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 1291771217-Ethylthio-9-fluoro-11beta-hydroxyandrosta-1,4,16-triene-3-one

Product 1

HCID 70562795(11beta)-16-Chloro-17-(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-oneYield 100.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344
Dichloromethane
Solvent

Procedure

A solution of 1.5 g of 17-(ethylthio)-9-fluoro-11β-hydroxyandrosta-1,4,16-trien-3-one in 70 ml of dry dichloromethane is stirred with 609 mg of N-chlorosuccinimide at room temperature under a nitrogen atmosphere for 2.5 hours. The resulting solution is diluted with 140 ml of chloroform; the chloroform solution is washed with saturated NaHCO3 solution and water, dried over anhydrous Na2SO4 and evaporated in vacuo to give 1.65 g of a foam. The foam is dissolved in chloroform-hexane (4:1) and chromatographed on a 60 g-silica gel column. Elution with chloroform-hexane (4:1) gives 1.2 g of a tlc-homogenous material. Crystallization from acetone-hexane gives 815 mg of an analytical specimen of the title compound, melting point 240°-241° C. (dec).

Workup

  1. washthe chloroform solution is washed with saturated NaHCO3 solution and water
  2. dry with materialdried over anhydrous Na2SO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-f36f854c903d4fd7a3e93dcd52a60942
Source dataset
uspto-grants-1981_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04265815

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes