Trifluoroacetic acid → HCID 59559669, compound
Reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29](=[O:46])[CH2:30][NH:31][C:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:36][CH:35]=2)=[O:33])[CH2:25][CH2:24]1)=[O:22])(C)(C)C>C(Cl)Cl>[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29](=[O:46])[CH2:30][NH:31][C:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:36][CH:35]=2)=[O:33])[CH2:25][CH2:24]1)=[O:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoroacetic acid (0.6 mL) was added to a stirred cold (0-5° C.) solution of [2-(4-{2-[(Biphenyl-4-carbonyl)-amino]-acetyl}-piperazine-1-carbonyl)-phenyl]-carbamic acid tert-butyl ester (90 mg, 0.165 mmol) in DCM (4 mL). Stirring was continued at same temperature for 4 hr. The mixture was quenched with DIPEA (1.1 ml) and cold water was then added and the product was extracted with DCM and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by column chromatography (using neutral alumina and 100% EtOAc as eluent) to afford 30 mg (40.8% yield) of biphenyl-4-carboxylic acid {2-[4-(2-amino-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 98.48%. 1H NMR (CDCl3): δ 7.9 (d, 2H), 7.68 (d, 2H), 7.62 (d, 2H), 7.5-7.4 (t, 3H), 7.4 (m, 1H), 7.3 (s, 1H), 7.2 (d, 1H), 7.08 (dd, 1H), 6.8-6.7 (m, 2H), 4.4 (s, 1H), 4.3 (d, 2H), 3.7 (d, 6H), 3.56 (t, 2H), 3.3 (s, 1H).