HCID 86738656, compound → HCID 86738657, compound
Reaction equation
C([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C:19]2([S:26][CH2:27][CH2:28][CH2:29][CH3:30])[S:23][CH2:24][CH3:25])[C@H:15]2[C@@:6]1([F:33])[C@:7]1([CH3:32])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:31])[CH:9]=[CH:8]1)(=O)C>CO.O1CCCC1>[CH2:27]([S:26][C:19]1([S:23][CH2:24][CH3:25])[CH2:18][CH2:17][C@H:16]2[C@H:15]3[C@:6]([F:33])([C@@H:5]([OH:4])[CH2:22][C@:20]12[CH3:21])[C@:7]1([CH3:32])[C:12](=[CH:11][C:10](=[O:31])[CH:9]=[CH:8]1)[CH2:13][CH2:14]3)[CH2:28][CH2:29][CH3:30]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
11β-Acetyloxy-17-(butylthio)-17-(ethylthio)-9-fluoroandrosta-1,4-diene-3-one (925 mg) is dissolved in a mixture of methanol (20 ml) and tetrahydrofuran (20 ml). The solution is stirred, purged with nitrogen and 3.0 M sodium hydroxide (3.0 ml) is added. After 2 hours a slight excess of acetic acid is added and the mixture is then concentrated in vacuo. It is diluted with water (150 ml) and extracted with chloroform. The chloroform extract is washed with water, dried (MgSO4 anh.) and evaporated to afford the title compound (870 mg). Examinations of the nmr spectrum and tlc behavior of this compound show the presence of some 17-(ethylthio)-9-fluoro-11β-hydroxyandrosta-1,4,16-triene-3-one and two 17-stereoisomers of the title compound. The material is applied on four 2.0 mm Merck silica gel plates and the plates are developed twice with chloroform-ethyl acetate (7:3). The products from the upper 1/3 and lower 2/3 of the broad band are isolated separately by extraction with chloroform-methanol (3:1 ) to afford respectively 340 and 527 mg of solids. One crystallization of the 340 mg of solid from ethyl acetate-hexane (1:1) and drying (100° C., 0.3 mm of Hg, 20 hours) gives the analytical specimen of the title compound (281 mg) melting point 118°-125° C. with consistent spectral data.