Trifluoroacetic acid → HCID 178461856, compound
Reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C@H:15]2[CH2:18][C@@H:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16]2)[C:13]2[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([O:19][C@@H:17]1[CH2:18][C@H:15]([N:14]2[C:13]3[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:12]=3[N:11]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])[CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of [(S)-1-[1-(cis-3-benzyloxycyclobutyl)-6-fluoro-1H-benzoimidazol-2-yl]ethyl]carbamic acid tert-butyl ester (570 mg, 1.3 mmol) in DCM (10 mL) was added TFA (4 mL) and the mixture stirred at RT for 1 h. The volatiles were removed in vacuo and the resulting residue dissolved in DCM and loaded onto SCX-2 (20 g). The cartridge was washed with DCM then MeOH and then 2M NH3 in MeOH solution. The relevant fractions were concentrated in vacuo to afford the title compound as yellow gum (320 mg, 73%). LCMS (Method J): RT 1.97 min [M+H]+ 340. 1H NMR (CDCl3, 400 MHz): δ 7.69-7.55 (2H, m), 7.44-7.24 (5H, m), 7.0 (1H, dt, J=11.8, 2.5 Hz), 4.81-4.66 (1H, m), 4.53 (2H, s), 4.32-4.21 (1H, m), 4.08-3.95 (1H, m), 3.02-2.75 (4H, m), 1.90 (2H, s, br), 1.50 (3H, d, J=7.0 Hz)-NMR: 328174