Dimethyl Sulfoxide → HCID 13421129, compound

HRID 1154301Notes

Reaction equation

HRID 1154301 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@@H:19]2[OH:23])[C@H:15]2[C@@:6]1([F:26])[C@:7]1([CH3:25])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:24])[CH:9]=[CH:8]1)(=[O:3])[CH3:2].O.[CH3:28][S:29]([CH3:31])=O>C(O)(=O)C.C(OC(=O)C)(=O)C>[C:1]([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@@H:19]2[O:23][CH2:28][S:29][CH3:31])[C@H:15]2[C@@:6]1([F:26])[C@:7]1([CH3:25])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:24])[CH:9]=[CH:8]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 13421127HCID 13421127, compound

Product 1

HCID 13421129HCID 13421129, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of (11β,17β)-11-(acetyloxy)-9-fluoro-17-hydroxyandrosta-1,4-dien-3-one (1.6 g, 4.42 mmole) in dry dimethylsulfoxide (30 ml), acetic acid (10 ml) and acetic anhydride (20 ml) were added. The starting steroid disappeared in 20 hours. The mixture was added into water and was extracted with chloroform (3×100 ml). The chloroform extracts were combined, washed with dilute brine and water, dried (anhydrous magnesium sulfate) and was evaporated in vacuo. The residue was dissolved in chloroform-hexane (1:1) and was absorbed on a column of silica gel (45 g). Elutions of the column successively with the same solvent mixture, chloroform and chloroform-ethyl acetate mixtures (2,3,5 and 10% ethyl acetate) gave (i) the homogeneous (tlc) title compound (1.1 g), (ii) a mixture of the 17α-isomer of the title compound and (11β)-11-(acetyloxy)-9-fluoroandrosta-1,4-dien-3,17-dione (300 mg), and (iii) (11β)-11-(acetyloxy)-9-fluoroandrosta-1,4-dien-3,17-dione (280 mg).

Workup

  1. extractionwas extracted with chloroform (3×100 ml)
  2. washwashed with dilute brine and water
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customwas evaporated in vacuo
  5. dissolutionThe residue was dissolved in chloroform-hexane (1:1)
  6. customwas absorbed on a column of silica gel (45 g)

Sources & evidence

ORD record
ord-1d79fc61512f4da5b7cc304dd40789d2
Source dataset
uspto-grants-1984_12
Patent number
US04488995

Reaction notes

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