Trifluoroacetic acid → (1R,2S,5R)-2-[[[(4S)-Hexahydro-1H-azepin-4-yl]amino]carbonyl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl hydrogen sulfate

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Reaction Steps

To a solution of N,N,N-tributylbutan-1-aminium {[((2S,5R)-2-{[(4S)-azepan-4-ylamino]carbonyl}-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl)oxy]sulfonyl}oxidanide (30.9 mg, 0.067 mmol) in anhydrous dichloromethane (7 mL) at 0° C. under nitrogen was added trifluoroacetic acid (0.5 mL, 6.5 mmol) dropwise. The reaction mixture was stirred for two hours then concentrated under vacuum. Ether was added to the residue and the resulting white precipitate was collected by centrifugation. The precipitate was purified by HPLC on a Phenomenex Synergy Polar-RP 80A column and lyophilized to afford the title compound as a white solid. LC-MS (negative ionization) m/e 361 (M−H); LC-MS (positive ionization) m/e 385 (M+Na); 1H NMR (600 MHz, D2O; unreferenced) (δ, ppm) 4.17 (1H, br d, J=3 Hz), 3.96-4.03 (2H, m), 3.27-3.38 (3H, m), 3.15-3.22 (2H, m), 3.02 (1H, d, J=12 Hz), 1.62-2.18 (m, 12H).

Provenance & Evidence