Tetrabutylammonium Fluoride → HCID 497415, compound

HRID 1167467Notes

Reaction equation

HRID 1167467 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][O:27][C:28]4[CH:32]=[CH:31][O:30][N:29]=4)[O:23][C:22]3=[O:33])=[CH:17][C:16]=2[F:34])[CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][O:27][C:28]4[CH:32]=[CH:31][O:30][N:29]=4)[O:23][C:22]3=[O:33])=[CH:17][C:16]=2[F:34])[CH:14]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53906022HCID 53906022, compound

Product 1

HCID 497415HCID 497415, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (0.59 g, 1.2 mmol) in anhydrous tetrahydrofuran (15 ml) was cooled to 0°. A solution of tetra-n-butylarnmonium fluoride (1 M, 5 ml, 5 mmol) was added and the mixture stirred 3 hours as the temperature rose to ambient. The mixture was evaporated to drvness, redissolved in dichloromethane (50 ml), washed with water (3×25 ml), and dried over magnesium sulfate. After filtration and evaporation the residue was purified by chromatography on a 10 g silica Mega Bond Elut® column. cluting with a gradient increasing in polarity from 0 to 10% MeOH in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (245 mg). MS (ESP): 375 (MH+) for C17H15FN4O5.

Workup

  1. customThe mixture was evaporated to drvness
  2. dissolutionredissolved in dichloromethane (50 ml)
  3. washwashed with water (3×25 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration and evaporation the residue
  6. customwas purified by chromatography on a 10 g silica Mega Bond Elut® column
  7. temperaturea gradient increasing in polarity from 0 to 10% MeOH in dichloromethane
  8. customevaporated

Sources & evidence

ORD record
ord-81b3eefae7b24882bae0fc65b38ff464
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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