Hydrochloric Acid → HCID 59621054, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of the amide 147 (5.5 g, 8.6 mmol) in dioxane (20 mL) at 23° C. was added a solution of 4 M HCl in dioxane (172 mL). The mixture was stirred for 4 h and concentrated in vacuo to afford crude, clear, viscous pale-yellow oil. A slurry of NaN3 (839 mg, 12.9 mmol) in pyridine (13 mL) was then cooled to 0° C. and trifluoromethanesulfonic anhydride (2.17 mL, 12.9 mmol) was added dropwise before allowing the mixture to warm to 23° C. and stir for 3 h. A solution of the amine hydrochloride 148 (4.22 g, 8.6 mmol) in H2O (6 mL) was then added followed by CuSO4.5H2O (321 mg, 1.29 mmol). The combined mixture was allowed to stir at 23° C. overnight. An aqueous saturated solution of NaHCO3 was then added and the organic layer was extracted 3×EtOAc. The combined organic extracts were washed 1×10% CuSO4, 2×1 M HCl, 1×brine, and dried over MgSO4. Solvents were removed in vacuo and the crude residue purified by flash chromatgraphy on silica gel using hexanes/ethyl actetate on a Biotage purification system yielding the azide 149 as a pale yellow, viscous oil (800 mg, 20%).

Provenance & Evidence