Sulfuric Acid → HCID 59200427, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tent-butyl 2-hydroxy-2,2-diphenylethylcarbamate (0.42 g, 1.39 mmol) in methanol (10 mL) was treated with concentrated sulfuric acid (2 mL). The reaction was stirred at 23° C. for a week and then at 40° C. for 2 hours. Solid sodium bicarbonate was added to the reaction until the pH reached ˜6-7 and the methanol was evaporated. The residue was then taken into ethyl acetate/water and the aqueous phase was extracted with ethyl acetate (3×). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified on preparative HPLC (ammonium acetate/acetonitrile/water) to give the title material (0.140 g, 46%). 1H NMR (400 MHz, CDCl3) δ: 3.11 (3H, s), 3.54 (2H, br s), 3.98 (2H, br s), 7.24-7.30 (2H, m), 7.31-7.36 (8H, m).

Provenance & Evidence