Trifluoroacetic acid → HCID 118379305, compound

Participants

Reaction Steps

Followed the general procedure for the acid mediated deprotection using (2R,3S)-3-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-2-(((R)-5-methyl-2-oxooxazolidin-3-yl)methyl)-4-oxoazetidine-1-sulfonic acid (92 mg, 0.133 mmol), DCM (1.33 mL) and TFA (615 μL, 7.98 mmol). The crude residue purified by reverse phase prep HPLC (XSelect CSH, 30×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 60 mL/min), affording the title compound (18.6 mg, 23%) as a white powder. LCMS: Rt=0.39 min, m/z=535.1 (M+1) Method 2m_acidic; 1H NMR (500 MHz, DMSO-d6) δ 9.29 (d, J=8.8 Hz, 1H), 6.85 (s, 1H), 5.22 (dd, J=8.8, 5.7 Hz, 1H), 4.55 (dt, J=13.5, 6.5 Hz, 1H), 4.15 (q, J=6.0 Hz, 1H), 3.72-3.63 (m, 2H), 3.34-3.27 (m, 2H), 1.46 (s, 3H), 1.42 (s, 3H), 1.28 (d, J=6.3 Hz, 3H).

Provenance & Evidence