Reaction Steps
Followed the general procedure for the acid mediated deprotection using (2R,3S)-3-((Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-2-((4-(((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)methyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidine-1-sulfonic acid (0.5 g, 0.48 mmol), DCM (2.5 mL), and TFA (1 mL, 13 mmol) for 1.5 h. The crude residue was purified by reverse phase prep HPLC (XSelect CSH, 30×100 mm, C18 column; ACN-water with 0.1% formic acid modifier, 60 mL/min) affording the title compound (123 mg, 42%). LCMS: Rt=0.31 min, m/z=587.2 (M+1) Method 2m_acidic; 1H NMR (400 MHz, DMSO-d6): δ 9.39 (br s, 1H), 7.76 (s, 1H), 7.22 (s, 2H), 6.73 (s, 1H), 5.33 (dd, J=9.0, 5.5 Hz, 1H), 4.84 (dd, J=14.3, 4.5 Hz, 1H), 4.73-4.61 (m, 1H), 4.61-4.48 (m, 1H), 4.27-4.14 (m, 2H), 3.02-2.89 (m, 3H), 2.85 (t, J=7.4 Hz, 3H), 1.85 (p, J=7.5 Hz, 3H) 1.32-1.04 (m, 6H); 1H NMR (400 MHz, D2O) δ 7.90 (s, 1H), 7.15 (s, 1H), 5.67 (d, J=5.5 Hz, 1H), 5.12-5.04 (m, 1H), 5.04-4.88 (m, 2H), 4.45 (s, 2H), 3.30-3.22 (m, 2H), 3.16 (t, J=7.6 Hz, 2H), 2.24-2.08 (m, 2H), 1.37-1.26 (m, 2H), 1.26-1.08 (m, 2H).
