Hydrogen Sulfide → 17beta-Ethylthio-9-fluoro-11beta-hydroxy-17alpha-mercaptoandrosta-1,4-diene-3-one
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].[SH2:26].B(F)(F)F.CCOCC>ClCCl.C(Cl)(Cl)Cl>[CH3:2][CH2:1][S:3][C@@:4]1([SH:26])[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]3Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -40 °C
Procedure
A solution of 2.0 g of 17-ethylthio-9-fluoro-11β-hydroxyandrosta-1,4,16-triene-3-one in dry dichloromethane (120 ml) was cooled and stirred in a bath at about -40° C. and a slow stream of hydrogen sulfide gas was passed into the solution while boron trifluoride etherate (1.2 ml) was added. After about 3.5 to 4.0 hours, the mixture was diluted with chloroform, warmed to room temperature and washed successively with a dilute sodium bicarbonate solution and water. The solution was dried (anhydrous magnesium sulfate), evaporated and the solid residue crystallized from ethyl acetate to afford 1.4 g of the title compound, melting point 239°-242° C.
Workup
- additionwas added
- temperaturewarmed to room temperature
- washwashed successively with a dilute sodium bicarbonate solution and water
- dry with materialThe solution was dried (anhydrous magnesium sulfate)
- customevaporated
- customthe solid residue crystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-9f6eb3123446479288bee69076f69062
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04435326
Reaction notes
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