Hydrogen Sulfide → 17beta-Ethylthio-9-fluoro-11beta-hydroxy-17alpha-mercaptoandrosta-1,4-diene-3-one

HRID 543465Notes

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]3

Participants

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 soluiton 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 soluiton was dried (anhydrous magnesium sulfate)
customevaporated
customthe solid residue crystallized from ethyl acetate
customto afford 1.4

Sources & evidence

ORD record: ord-449562b410bc4fbd8e5e841defa7045c
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04446071

Reaction notes

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