Trifluoroacetic acid → HCID 118379523, compound

Participants

Reaction Steps

Followed the general procedure for the acid mediated deprotection using (3S,4R)-3-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-2-oxo-4-((2-oxopyrrolidin-1-yl)methyl)azetidine-1-sulfonic acid (55 mg, 0.072 mmol), DCM (720 μL) and TFA (333 μL, 4.32 mmol). The crude residue was purified by reverse phase preperative HPLC (XSelect CSH, 19×100 mm, 5 μm, C18 column; ACN-water with 0.1% formic acid modifier, 24 mL/min), affording the title compound (6 mg, 16%) as a white solid. LCMS: Rt=0.35 min, m/z=519.0 (M+1) Method 2m_acidic; 1H NMR (400 MHz, D2O): δ 7.17 (s, 1H), 5.46 (d, J=5.8 Hz, 1H), 4.71-4.64 (m, 1H), 3.92 (dd, J=14.7, 8.7 Hz, 1H), 3.71-3.55 (m, 2H), 3.49 (dd, J=14.7, 4.1 Hz, 1H), 2.42 (td, J=8.0, 4.8 Hz, 2H), 2.08 (p, J=7.6 Hz, 2H), 1.55 (s, 3H), 1.54 (s, 3H).

Provenance & Evidence