Potassium Carbonate → HCID 70520810, compound

HRID 1649337Notes

Reaction equation

HRID 1649337 reaction equation
[FH:1].[F:2][CH:3]([F:24])[C@H:4]1[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C:20](=[CH:21][CH2:22][C@:5]12[CH3:6])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:23])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3.[Cl:25]N1C(=O)CCC1=O.C(=O)([O-])[O-].[K+].[K+]>O.C(Cl)Cl.C1COCC1>[Cl:25][C@:20]12[C@@H:21]([F:1])[CH2:22][C@@:5]3([CH3:6])[C@@H:7]([CH2:8][CH2:9][C@@H:4]3[CH:3]([F:24])[F:2])[C@@H:10]1[CH2:11][CH2:12][C:13]1[C@:18]2([CH3:19])[CH2:17][CH2:16][C:15](=[O:23])[CH:14]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14917Hydrofluoric AcidHCID 31398ChlorosuccinimideHCID 54301910HCID 54301910, compound

Product 1

HCID 70520810HCID 70520810, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.9 ml of liquid hydrogen fluoride and 2.0 ml of THF previously cooled to -78° under nitrogen is added a solution of 17b-difluoroandrosta-4,9(11)-dien-3-one (XI, Example 5, 1.5 g) with 10-15 ml of methylene chloride. After termal equilibrium is obtained, solid N-chlorosuccinimide (0.8 g) is added and the mixture stirred at -78° for approximately 3 hrs. The mixture is warmed to -20° over a 25 min period and then warmed to 0° over the next 30 min and then poured slowly into an ice-cooled solution of potassium carbonate (15 g) and water (50 ml). The phases are separated and the aqueous phase is washed twice with methylene chloride. The organic phases are combined and washed with a solution of sodium sulfite (2.5 g in 30 ml), dried over sodium sulfate and concentrated under reduced pressure to give a solid which is purified by column chromatography to give the title compound.

Workup

  1. customAfter termal equilibrium is obtained
  2. temperatureThe mixture is warmed to -20° over a 25 min period
  3. temperaturewarmed to 0° over the next 30 min
  4. customThe phases are separated
  5. washthe aqueous phase is washed twice with methylene chloride
  6. washwashed with a solution of sodium sulfite (2.5 g in 30 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a solid which
  10. customis purified by column chromatography

Sources & evidence

ORD record
ord-616848597a2749c6a2f705caa3930f30
Source dataset
uspto-grants-1983_11
Patent number
US04416822

Reaction notes

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