p-Toluenesulfonic acid → HCID 18930726, compound

Reaction equation

C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=2)[C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9]1)C1C=CC=CC=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([OH:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1>[Pd].CO>[N:11]1([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=2)[C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1.[C:24]1([CH3:34])[CH:25]=[CH:26][C:27]([S:30]([OH:33])(=[O:31])=[O:32])=[CH:28][CH:29]=1

Participants

Procedure

A mixture of 120c (2.6 g, 8.5 mmol), p-toluene sulfonic acid (1.6 g, 8.5 mmol), 10% Pd/C (0.52 g) and MeOH (40 mL) were shaken on a Parr hydrogenation apparatus at 49 psi of H2. After TLC indicated complete reaction, the catalyst was removed by filtration through a Celite pad, and solvent was evaporated to yield a white solid (3.3 g). IR(KBr): cm-1 3416, 1724. 1H NMR(300 MHz, CDCl3): 8.70 (br, 1H), 7.51-7.28 (m, 6H), 7.12 (d, 2H, J=8 Hz), 4.10 (br, 1H), 3.85 (s, 3H), 3.41-3.24 (m, 8H), 2.29 (s, 3H). HR-MS: Calc'd. 221.1290, Found 221.1294.