Tetrahydrofuran → HCID 13276352, compound

HRID 904861Notes

Reaction equation

HRID 904861 reaction equation
C([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][C:18](=[O:27])[C:19]2([S:25][CH3:26])[S:23][CH3:24])[C@H:15]2[C@@:6]1([F:30])[C@:7]1([CH3:29])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:28])[CH:9]=[CH:8]1)(=O)C.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:30][C@:6]12[C@@H:5]([OH:4])[CH2:22][C@@:20]3([CH3:21])[C@@H:16]([CH2:17][C:18](=[O:27])[C:19]3([S:23][CH3:24])[S:25][CH3:26])[C@@H:15]1[CH2:14][CH2:13][C:12]1[C@:7]2([CH3:29])[CH:8]=[CH:9][C:10](=[O:28])[CH:11]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 13276350HCID 13276350, compound

Product 1

HCID 13276352HCID 13276352, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 1.7 g (3.76 mmole) of 11β-(acetyloxy)-9-fluoro-17,17-bis(methylthio)androsta-1,4-diene-3,16-dione in a mixture of methanol (70 ml), tetrahydrofuran (50 ml) and water (5 ml) was added 10% potassium carbonate solution dropwise until the pH of solution was about 10. The solution was allowed to stir at room temperature under nitrogen for 2 hours and quenched with a slight excess of concentrated acetic acid. The solvent was evaporated in vacuo to give a slurry. This was diluted with water and extracted with dichloromethane. The dichloromethane solution was dried over anhydrous Na2SO4 and evaporated in vacuo to give 1.35 g of the title compound. Recrystallization of this from acetone-hexane gave 720 mg of an analytical specimen, melting point 293°-294° C., dec.

Workup

  1. customquenched with a slight excess of concentrated acetic acid
  2. customThe solvent was evaporated in vacuo
  3. customto give a slurry
  4. extractionextracted with dichloromethane
  5. dry with materialThe dichloromethane solution was dried over anhydrous Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c5575509aeef422d9ea732b16c40a26e
Source dataset
uspto-grants-1983_12
Patent number
US04420428

Reaction notes

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