Trifluoroacetic acid → HCID 66744529, compound

Participants

Reaction Steps

To a solution of (1R,5S)-3-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid (30 mg, 0.04 mmol) in DCM (0.3 mL) was added TFA (500 μL, 6.50 mmol) and reaction was stirred at room temperature for 2 h. The solvent was removed under reduced pressure and the residue was dissolved in DMSO, filtered and purified via reverse phase HPLC using a gradient of 10 to 99% MeOH—H2O (TFA modifier) to obtain (1R,5S)-3-[5-amino-6-[5-[4-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid. LC/MS m/z 408.4 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.85 (s, 2H), 8.17 (d, J=8.2 Hz, 2H), 7.91 (s, 1H), 7.73 (d, J=8.2 Hz, 2H), 6.77 (s, 2H), 4.26 (t, J=5.7 Hz, 2H), 3.87 (d, J=10.4 Hz, 2H), 3.47-3.46 (m, 2H), 2.63 (t, J=5.2 Hz, 3H), 2.19 (s, 2H), 1.49 (t, J=2.9 Hz, 1H).

Provenance & Evidence