Tetrabutylammonium Fluoride → HCID 68545903, compound

HRID 1446101Notes

Reaction equation

HRID 1446101 reaction equation
C([SiH2][O:6][C:7](C)(C)[CH:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][C:23]([N:26]4[CH2:32][CH2:31][CH2:30][N:29]([CH2:33][C:34]5([CH3:45])[O:38][C:37]6=[N:39][C:40]([N+:42]([O-:44])=[O:43])=[CH:41][N:36]6[CH2:35]5)[CH2:28][CH2:27]4)=[N:24][CH:25]=3)=[C:16]([F:46])[CH:15]=2)[CH2:9]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[F:46][C:16]1[CH:15]=[C:14]([N:10]2[CH2:9][CH:8]([CH2:7][OH:6])[O:12][C:11]2=[O:13])[CH:19]=[CH:18][C:17]=1[C:20]1[CH:25]=[N:24][C:23]([N:26]2[CH2:32][CH2:31][CH2:30][N:29]([CH2:33][C:34]3([CH3:45])[O:38][C:37]4=[N:39][C:40]([N+:42]([O-:44])=[O:43])=[CH:41][N:36]4[CH2:35]3)[CH2:28][CH2:27]2)=[N:22][CH:21]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131727903HCID 131727903, compound

Product 1

HCID 68545903HCID 68545903, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(3-fluoro-4-{2-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-[1,4]diazepan-1-yl]-pyrimidin-5-yl}-phenyl)-oxazolidin-2-one (580 mg, 0.84 mmol) in THF (8.0 mL) was added TBAF (3.3 mL, 3.3 mmol, 1.0 M in THF). The mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc, washed with brine, dried with Na2SO4, purified by flash chromatography to give the title product (100 mg, 21%) as a yellow solid. ESI MS m/z 569 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.60 (dd, J=30, 3.0 Hz, 1H), 7.36 (t, J=20 Hz, 1H), 7.29 (d, J=3.0 Hz, 1H), 7.25 (s, 2H), 4.70 (m, 1H), 4.10 (d, J=25.0 Hz, 1H), 3.95-4.06 (m, 2H), 3.82-3.88 (m, 2H), 3.76 (d, J=23.0 Hz, 1H), 3.64 (dd, J=33, 10.0 Hz, 1H), 3.41-3.58 (m, 2H), 3.31 (bs, 3H), 3.02 (d, J=38.0, 1H), 2.94 (q, J=16.0 Hz, 1H), 2.82-2.84 (m, 1H), 2.70-2.78 (m, 1H), 2.60 (d, J=38.0, 1H), 1.64-1.72 (m, 1H), 1.50-1.58 (m, 1H), 1.48 (s, 3H).

Workup

  1. washwashed with brine
  2. dry with materialdried with Na2SO4
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9221c85213174be8aa2794f517295c41
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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