Sodium Bicarbonate → [5-(5-{1-[4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazol-2-yl]methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazol-2-yl]-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (1.95 g) in acetic acid (20 mL) was added ammonium acetate (3.41 g), and the mixture was stirred at 110° C. for 30 min. The reaction mixture was cooled to room temperature, and neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a crude product (1.9 g). To a solution of the obtained crude product in tetrahydrofuran (10 mL) was added tetrabutylammonium fluoride (1M tetrahydrofuran solution) (5 mL) at room temperature. The reaction mixture was stirred at room temperature for 10 min and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (1.0 g, yield 81%) was obtained as white crystals from a fraction eluted with ethyl acetate. melting point 199-201° C. MS: 448 (MH+).

Provenance & Evidence