Acetic Acid → HCID 57736427, compound

Participants

Reaction Steps

To a solution of N-[[2-(tert-butyldiphenylsilyloxy)ethoxy]methyl]-5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxamide (56 mg, 0.076 mmol) and acetic acid (5 μl, 0.091 mmol) in tetrahydrofuran (5 ml), tetrabutylammonium fluoride (1 M tetrahydrofuran solution) (91 μl, 0.091 mmol) was added, and the mixture was stirred for 6 hours at room temperature. Acetic acid (5 μl, 0.091 mmol) and tetrabutylammonium fluoride (1 M tetrahydrofuran solution) (91 μl, 0.091 mmol) were further added to the reaction solution, and the mixture was stirred for 16 hours at room temperature. Acetic acid (5 μl, 0.091 mmol) and tetrabutylammonium fluoride (1 M tetrahydrofuran solution) (91 μl, 0.091 mmol) were further added to the reaction solution, and the mixture was stirred for 5 hours at room temperature. Saturated aqueous ammonium chloride was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, subsequently dried over anhydrous sodium sulfate, and filtered, and then the filtrate was concentrated under reduced pressure. The resulting concentration residue was subjected to flash silica gel column chromatography, and the fraction obtained from an elution with 70% ethyl acetate/hexane was concentrated under reduced pressure. Ether was added to the resulting concentration residue to precipitate a solid, and ether was distilled off to obtain the title compound (35 mg, 0.071 mmol, 93%) as a white solid.

Provenance & Evidence