HCID 131733498, compound → HCID 130473053, compound

Participants

Reaction Steps

To a solution of [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]thiophene-2-carboxylate (400 mg, 0.65 mmol) in pyridine (6 mL) was added HF.pyridine (0.88 ml) dropwise and the mixture was allowed to stir at room temperature for 3 h. The mixture was cooled to 0° C. and quenched with saturated aqueous sodium bicarbonate solution (10 mL). The mixture was extracted with ethyl acetate (3×30 mL) and the combined organic fractions were passed through a hydrophobic fit and the solvent was removed by evaporation under reduced pressure. The crude material was purified by silica gel column chromatography, eluting with 0-100% ethyl acetate/10% methanol in ethyl acetate, to afford the title compound (323 mg, quantitative yield) as a white solid.

Provenance & Evidence