Tetrabutylammonium Fluoride → N-[((5S)-3-{2-Fluoro-4'-[5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide

HRID 747220Notes

Reaction equation

HRID 747220 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][NH:33][C:34](=[O:36])[CH3:35])[O:29][C:28]4=[O:37])=[CH:23][C:22]=3[F:38])=[CH:17][CH:16]=2)[CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:38][C:22]1[CH:23]=[C:24]([N:27]2[CH2:31][C@H:30]([CH2:32][NH:33][C:34](=[O:36])[CH3:35])[O:29][C:28]2=[O:37])[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 59749422N-[((5S)-3-{4'-[5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-2-fluoro-1,1'-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide

Product 1

HCID 59749464N-[((5S)-3-{2-Fluoro-4'-[5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]-1,1'-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamideYield 29.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-[((5S)-3-{4′-[5-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4,5-dihydroisoxazol-3-yl]-2-fluoro-1,1′-biphenyl-4-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide (164 mg, 0.3 mmol) was dissolved in tetrahydrofuran (5 ml) at room temperature. A solution of tetrabutylammonium fluoride in tetrahydrofuran (1M; 0.3 ml, 0.3 mmol) was added and the reaction mixture stirred for 30 minutes. The solvent was removed in vacuo then dichloromethane (2 ml) added. Purification by chromatography (SiO2 10 g bond elut; 0 to 6% methanol/dichloromethane) yielded a white solid. This was washed with water (50 ml) to yield 37.9 mg (29%) of the desired compound.

Workup

  1. customThe solvent was removed in vacuo
  2. additiondichloromethane (2 ml) added
  3. customPurification by chromatography (SiO2 10 g bond elut; 0 to 6% methanol/dichloromethane)
  4. customyielded a white solid
  5. washThis was washed with water (50 ml)

Sources & evidence

ORD record
ord-b9a674cf5c82470691caae697e6ad91f
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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