Tetrabutylammonium Fluoride → 8-Fluoro-4-(2-hydroxyethyl)-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide

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Reaction Steps

To a solution of 4-[2-(tert-butyldimethylsilanyloxy)ethyl]-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide from Example 21F (0.34 mmol) in THF (5.0 ml) was added a solution of tetrabutylammonium fluoride in THF (1.0 M, 1.0 ml, 1.0 mmol) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 3 days. The mixture was evaporated in vacuo and the residue was taken up in CH2Cl2 and washed with ammonium chloride solution. The organic phase was dried and evaporated in vacuo and the residue was purified by flash chromatography on silica (eluant CHCl3:methanol 95:5) to give a white solid; yield 120 mg, 64%.

Provenance & Evidence