Tetrabutylammonium Fluoride → HCID 59350551, compound

HRID 747218Notes

Reaction equation

HRID 747218 reaction equation
[Si]([O:8][CH2:9][CH:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:31][C@H:30]([CH2:32][N:33]5[CH:37]=[C:36]([CH3:38])[N:35]=[N:34]5)[O:29][C:28]4=[O:39])=[CH:23][C:22]=3[F:40])=[CH:17][CH:16]=2)[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:40][C:22]1[CH:23]=[C:24]([N:27]2[CH2:31][C@H:30]([CH2:32][N:33]3[CH:37]=[C:36]([CH3:38])[N:35]=[N:34]3)[O:29][C:28]2=[O:39])[CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH2:11][CH:10]([CH2:9][OH:8])[O:14][N:13]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59749428HCID 59749428, compound

Product 1

HCID 59350551HCID 59350551, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(5R)-3-{4′-[5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-2-fluoro-1,1′-biphenyl-4-yl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (283 mg, 0.5 mmol) was dissolved in tetrahydrofuran (5 ml) at room temperature. A 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.5 ml, 0.5 mmol) was added and the reaction mixture stirred for 30 minutes. The solvent was removed in vacuo then dichloromethane (50 ml) added. This was washed with water (50 ml), separated, dried (magnesium sulfate), filtered then concentrated in vacuo onto silica (2 ml). This was then subjected to chromatography (silica gel 10 g bond elut; 0 to 6% methanol/dichloromethane) to yield 150 mg (66%) of the desired compound.

Workup

  1. customThe solvent was removed in vacuo
  2. additiondichloromethane (50 ml) added
  3. washThis was washed with water (50 ml)
  4. customseparated
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationthen concentrated in vacuo onto silica (2 ml)

Sources & evidence

ORD record
ord-693bed3bd89f4991987fd32139e83c44
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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