Trifluoroacetic acid → HCID 14828033, compound
Reaction equation
[NH:1]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:2]([C:18]([NH:20][C@H:21]([C:37]([O:39][CH3:40])=[O:38])[CH2:22][CH2:23][CH2:24][CH2:25][NH:26]C(OCC1C=CC=CC=1)=O)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C=CC=CC=1)=O.FC(F)(F)C(O)=O>CO>[NH:1]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:2]([C:18]([NH:20][C@H:21]([C:37]([O:39][CH3:40])=[O:38])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dilysine 10 (7.43 g, 0.0113 mol) was dissolved in MeOH (100 mL). After being purged with nitrogen, 10% Pd/C (0.30 g) was added. The flask was then purged with hydrogen and the reaction mixture was stirred for overnight. The Pd/C was removed by filtration through a pad of celite. Trifluoroacetic acid (TFA, 1.8 mL, 0.023 mol) was added into the filtrate and then the solvent was removed in vacuo to give viscous oil. A white gluey substance was obtained by triturating with 20 mL diethyl ether. The resulting substance was dried in vacuo to give the glassy solid product 11 (6.4 g, 92%): 1H NMR (500 MHz, d6 DMSO) δ 8.19 (d, J=7.5, 1 H), 7.90 (br s, 6H), 6.82 (d, J=8.0, 1 H), 4.23 (m, 1H), 3.91 (m, 1H), 3.61 (s, 3H), 2.75 (m, 4H), 1.36-1.61 (m, 21H); 13C NMR (125 MHz, d6 DMSO) δ 172.4 (2), 158.4 (q, 2), 155.3, 117.2 (q, 2), 78.0, 53.9, 51.6, 38.7, 38.6, 31.2, 30.3, 28.1 (3), 26.7, 26.5, 22.3, 22.2; HRMS (FAB) m/z calcd for C22H38F6N4O9 (M+H)+ 389.2764, found 389.2767.