HCID 86739402, compound → HCID 15586553, compound

HRID 543852Notes

Reaction equation

HRID 543852 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:15]3(SCC(OCC)=O)[S:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:36])[CH:4]=[CH:5][C:6](=[O:35])[CH:7]=1>C(C1C=CC=CC=1CC)C.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][CH:14]=[C:15]3[S:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:36])[CH:4]=[CH:5][C:6](=[O:35])[CH:7]=1

Participants

4

Reactant 1

HCID 86739402HCID 86739402, compound

Product 1

HCID 15586553HCID 15586553, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 86571,2-DiethylbenzeneSolvent

Procedure

A solution of (11β)-2,2'-[(9-fluoro-11-hydroxy-3-oxoandrosta-1,4-dien-17,17-diyl)bis(thio)]bisacetic acid, diethyl ester (6.48 g; see example 2) in dry diethylbenzene (200 ml) was refluxed in contact with air for 4.0 hours. The solution was then cooled, diluted with some chloroform and was poured on a column of silica gel (60 g), eluting the column successively with chloroform and chloroform-ethyl acetate (95:5, 9:1 and 4:1) to isolate the title compound (4.15 g). One crystallization of this from ethyl acetate-hexane gave the analytical specimen of the title compound (3.8 g), melting point 144°-145° C., with consistent spectral data.

Workup

  1. temperatureThe solution was then cooled
  2. additionwas poured on a column of silica gel (60 g)
  3. washeluting the column successively with chloroform and chloroform-ethyl acetate (95:5, 9:1 and 4:1)

Sources & evidence

ORD record
ord-1b14ad0075874faa924ce7b400703672
Source dataset
uspto-grants-1984_05
Patent number
US04447363

Reaction notes

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