반응 단계
3-({2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid (intermediate XI, 15.0 mg, 0.028 mmol) was taken up in HCl(g) saturated EtOAc (1 mL). After 30 min, it was concentrated under a flow of nitrogen to give 3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(methylsulfonyl)(propyl)amino]benzoic acid as a white solid which was then taken up in DMF (800 μL) with BOP reagent (15.0 mg, 0.033 mmol), ethyl(diisopropyl)amine (12.0 μL, 0.069 mmol), and (1,1-dimethylprop-2-yn-1-yl)amine (23.0 mg, 0.276 mmol). After sitting at RT for 5 hr, the reaction was purified by preparative HPLC (5->95% CH3CN/H2O, 0.1% added TFA, C18 PRO YMC 20×150 mm) to afford 3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-N-(1,1-dimethylprop-2-yn-1-yl)-5-[(methylsulfonyl)(propyl)amino]benzamide as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.81 (br s, 3H), 7.77 (s, 1H), 7.69 (s, 1H), 7.47 (s, 1H), 7.35-7.27 (m, 3H), 7.22-7.16 (m, 2H), 6.89 (s, 1H), 4.61 (A of AB, d, J=11.7 Hz, 1H), 4.54 (B of AB, d, J=11.7 Hz, 1H), 3.64 (t, J=7.1 Hz, 2H), 3.51 (A of AB, d, J=9.8 Hz, 1H), 3.45 (B of AB, d, J=9.8 Hz, 1H), 3.17 (A of AB, d, J=13.2 Hz, 1H), 3.00 (B of AB, d, J=13.2 Hz, 1H), 2.86 (s, 3H), 1.75 (s, 6H), 1.54-1.44 (m, 2H), 1.32 (s, 3H), 1.27 (s, 3H), 0.89 (t, J=7.3 Hz, 3H).
