Tetrabutylammonium Fluoride → HCID 59063640, compound
Reaction equation
C([Si](C)(C)[O:6][C@H:7]([C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[N:29][CH:30]=1)[CH2:8][NH:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([CH3:24])[S:22][CH:23]=2)=[CH:15][CH:14]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:6][C@H:7]([C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[N:29][CH:30]=1)[CH2:8][NH:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:20]=[C:21]([CH3:24])[S:22][CH:23]=2)=[CH:17][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (R)-N-[5-(1-(tert-butyl-dimethyl-silanyloxy)-2-{2-[4-(2-methyl-thiazol-4-yl)-phenoxy]-ethylamino}-ethyl)-pyridin-2-yl]-acetamide (115 mg, 0.218 mmol) in tetrahydrofuran (1.5 mL) was added tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 0.65 mL, 0.65 mmol) at room temperature. The resulting solution was allowed to stir for about two and one-half hours, and the reaction mixture was then partitioned between ethyl acetate and water. The pH of the mixture was adjusted to about 10-11, and the aqueous phase was then extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude material was purified by column chromatography (methylene chloride to 20% methanol/methylene chloride) to afford 75 mg (83%) of the desired product. LRMS ([M+1]+): 413.2.