Potassium Fluoride → HCID 58392648, compound

HRID 446842Notes

Reaction equation

HRID 446842 reaction equation
[CH:1]([O:3][C:4]([N:6]1[CH2:30][C@:29]2([C:31](=[O:38])[CH2:32]OS(C)(=O)=O)[C@@H:8]([CH2:9][C@H:10]3[C@H:23]4[C@@:14]([F:27])([C@:15]5([CH3:26])[C:20]([C@@H:21]([F:24])[CH2:22]4)=[CH:19][C:18](=[O:25])[CH:17]=[CH:16]5)[C@@H:13]([OH:28])[CH2:12][C@@:11]32[CH3:39])[CH2:7]1)=[O:5])=[CH2:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-:57].[F-].[K+]>C1COCC1>[CH:1]([O:3][C:4]([N:6]1[CH2:30][C@:29]2([C:31](=[O:38])[CH2:32][F:57])[C@@H:8]([CH2:9][C@H:10]3[C@H:23]4[C@@:14]([F:27])([C@:15]5([CH3:26])[C:20]([C@@H:21]([F:24])[CH2:22]4)=[CH:19][C:18](=[O:25])[CH:17]=[CH:16]5)[C@@H:13]([OH:28])[CH2:12][C@@:11]32[CH3:39])[CH2:7]1)=[O:5])=[CH2:2]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 2724141Tetrabutylammonium FluorideHCID 58392718HCID 58392718, compound

Product 1

HCID 58392648HCID 58392648, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 165 (774 mg, 1.359 mmol), TBAF 1M in THF (2038 μl, 2.038 mmol) and potassium fluoride (79 mg, 1.359 mmol) in dry THF (25 ml) is stirred under nitrogen at r.t. for 2 hours, then at reflux for 1 hour 30 minutes. The mixture is partitioned between AcOEt and water, then the aqueous phase is extracted with AcOEt; the combined organic layers are washed with brine, dried over Na2SO4 and filtered. The solvent is evaporated to give an orange oil which is purified by silica gel chromatography (eluent: DCM/MeOH 98/2) to give the title compound (185 mg, 27.6% yield).

Workup

  1. temperatureat reflux for 1 hour 30 minutes
  2. customThe mixture is partitioned between AcOEt and water
  3. extractionthe aqueous phase is extracted with AcOEt
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent is evaporated
  8. customto give an orange oil which
  9. customis purified by silica gel chromatography (eluent: DCM/MeOH 98/2)

Sources & evidence

ORD record
ord-7490058dc32a4a368bc6ab6a10efe626
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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