Tetrabutylammonium Fluoride → HCID 71543441, compound

Participants

Reaction Steps

N-(4-(3-((tert-butyldimethylsilyl)oxy)propyl)phenyl)-4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutylbenzenesulfonamide (276.8 mg, 0.472 mmol) was dissolved in Tetrahydrofuran (THF) (10 mL). To this solution was added TBAF in THF (1M) (0.707 mL, 0.707 mmol), and the solution was left to stir for 1 hr at room temperature. The reaction mixture was concentrated on the Biotage V10 evaporator, extracted to the organic phase of an aqueous workup between ethyl acetate (10 mL) and water (10 mL) followed by a brine (10 mL) wash. The organic phase was passed through a hydrophobic frit, and concentrated in vacuo, before being dissolved in DCM and loaded onto a silica column and purified by column chromatography on Biotage II Flashmaster (20 g silica (Si), 40 mins, 0-50% EtOAc in cyclohexane). The relevant fractions were combined and condensed and the sample was freeze dried using a minimum of dioxane in water, to give the final product, 67%. LCMS (M+1) 473.1, RT 1.16 mins.

Provenance & Evidence