Water → HCID 13276360, compound

HRID 904863Notes

Reaction equation

HRID 904863 reaction equation
C([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][C:18](=[O:29])[C:19]2([S:26][CH2:27][CH3:28])[S:23][CH2:24][CH3:25])[C@H:15]2[C@@:6]1([F:32])[C@:7]1([CH3:31])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:30])[CH:9]=[CH:8]1)(=O)C.[OH-].[Na+].O>CO.O1CCCC1>[CH2:27]([S:26][C:19]1([S:23][CH2:24][CH3:25])[C:18](=[O:29])[CH2:17][C@H:16]2[C@H:15]3[C@:6]([F:32])([C@@H:5]([OH:4])[CH2:22][C@:20]12[CH3:21])[C@:7]1([CH3:31])[C:12](=[CH:11][C:10](=[O:30])[CH:9]=[CH:8]1)[CH2:13][CH2:14]3)[CH3:28]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13276358HCID 13276358, compound

Product 1

HCID 13276360HCID 13276360, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

11β-(Acetyloxy)-17,17-bis(ethylthio)-9-fluoroandrosta-1,4-diene-3,16-dione was dissolved in a mixture of methanol (3.0 ml) and tetrahydrofuran (3.0 ml) and was exposed to 3 M sodium hydroxide (0.3 ml) for 1.0 hour under an atmosphere of nitrogen. The mixture was then added to water and was extracted with chloroform. The chloroform solution was washed with water, dried (MgSO4) and was evaporated to afford the title compound as a solid (80 mg). One crystallization of this form ethyl acetate-hexane followed by drying gave the analytical specimen of the title compound (58 mg), melting point 268°-270° C. (dec., discoloration starts from ca. 200° C.).

Workup

  1. extractionwas extracted with chloroform
  2. washThe chloroform solution was washed with water
  3. dry with materialdried (MgSO4)
  4. customwas evaporated

Sources & evidence

ORD record
ord-363cb6e7af1f4a51881ee1926000d436
Source dataset
uspto-grants-1983_12
Patent number
US04420428

Reaction notes

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