Potassium Carbonate → HCID 53882777, compound

HRID 1440971Notes

Reaction equation

HRID 1440971 reaction equation
[FH:1].[NH:2]([C:6]1[C:23](=[O:24])[C@@H:22]2O[CH:21]2[C@@:20]2([CH3:26])[C:7]=1[CH:8]=[CH:9][C@@H:10]1[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]1[CH2:12][CH2:13][C:14]2=[O:27])[C:3]([CH3:5])=[O:4].F.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(Cl)(Cl)Cl>[C:3]([NH:2][C:6]1[C:23](=[O:24])[C:22]([F:1])=[CH:21][C@@:20]2([CH3:26])[C:7]=1[CH:8]=[CH:9][C@@H:10]1[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]1[CH2:12][CH2:13][C:14]2=[O:27])(=[O:4])[CH3:5]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 14917Hydrofluoric AcidHCID 22859494HCID 22859494, compoundHCID 69735124Hydrogen fluoride tetrahydrofuranHCID 178435160HCID 178435160, compound

Product 1

HCID 53882777HCID 53882777, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent4×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of anhydrous hydrogen fluoride (6 g) in tetrahydrofuran (11.8 g) and chloroform (6 ml) contained in a screw-capped polyethylene bottle chilled to about -60° C. was added a solution of 4-acetamino-1,2α-epoxy-androsta-4,6-diene-3,17-dione (3.554 g, 10 mmol) in chloroform (30 ml) likewise chilled to about -60° C. The hydrogen fluoride-tetrahydrofuran reagent was immersed in an acetone-dry ice bath while the steroid was being added. Additional chloroform (6 ml) was used to aid the transfer of the epoxide. Subsequently the reaction mixture was maintained at -30° C. for 4 h and then added gradually to a well agitated mixture of an aqueous solution of potassium carbonate, chloroform and ice. The organic layer was separated, the alkaline aqueous layer back-extracted twice with chloroform and the combined organic layers were evaporated to dryness. The residue was submitted to flash chromatography with ethyl acetate-ethanol to give pure 4-acetylamino-2-fluoroandrosta-1,4,6-triene-3,17-dione in 70% yield (2.502 g).

Workup

  1. temperaturelikewise chilled to about -60° C
  2. additionwas being added
  3. temperatureSubsequently the reaction mixture was maintained at -30° C. for 4 h
  4. additionadded gradually to a well
  5. customThe organic layer was separated
  6. extractionthe alkaline aqueous layer back-extracted twice with chloroform
  7. customthe combined organic layers were evaporated to dryness

Sources & evidence

ORD record
ord-ae685ad406ba415f868d88549dfe3abf
Source dataset
uspto-grants-1996_03
Patent number
US05502044

Reaction notes

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