反应详情

A solution of the N-Boc-protected amine 13B (300 mg, 0.763 mmol) in CH2Cl2 (3 mL) and TFA (3 mL) was stirred at rt for 1 h. The solution was then concentrated under reduced pressure and the residue azeotroped with a 1:1 solution of CH2Cl2/toluene (3×10 mL) and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, CH2Cl2/CH3OH, 100:0 to 80:20 gradient) to afford the title compound (71 mg) as a white solid. 1H NMR (DMSO-d6) δ 2.21 (s, 3H), 3.12 (s, 3H), 5.16 (d, J=2.2 Hz, 1H), 5.39 (d, J=2.2 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H), 7.98 (d, J=8.3 Hz, 1H); 13C NMR (DMSO-d6) δ 15.70, 26.73, 95.59, 113.18, 115.83, 128.79, 132.09, 136.03, 136.37, 136.54, 136.68, 151.88, 160.56; HPLC a) column: Phenominex C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.70 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.59 min retention time (98%).

1. concentrationThe solution was then concentrated under reduced pressure
2. customthe residue azeotroped with a 1:1 solution of CH2Cl2/toluene (3×10 mL)
3. concentrationconcentrated under reduced pressure
4. customThe residue was purified by flash chromatography (silica gel, CH2Cl2/CH3OH, 100:0 to 80:20 gradient)