C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:36])[CH2:21][NH:22][CH:23]2[CH2:31][C:30]3[C:25](=[C:26]([O:34][CH3:35])[CH:27]=[CH:28][C:29]=3[O:32][CH3:33])[CH2:24]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1.[ClH:37].C(OCC)C>CO.[Pd]>[ClH:37].[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:36])[CH2:21][NH:22][CH:23]2[CH2:31][C:30]3[C:25](=[C:26]([O:34][CH3:35])[CH:27]=[CH:28][C:29]=3[O:32][CH3:33])[CH2:24]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2(R)-8-Benzyloxy-5-[2-(4,7-dimethoxy-indan-2-ylamino)-1-hydroxy-ethyl]-1H-quinolin-2-one (37 mg, 0.08 mmol) is dissolved in methanol (10 mL) and the compound is deprotected by adding a catalytic amount of 10% palladium on charcoal and placing the solution under an atmosphere of hydrogen. The reaction is shown to be complete by TLC after 4 hours. The catalyst is filtered off, 1M HCl/diethyl ether (1.1 equivalent) is added and the solvent is removed in vacuo. TLC (silica, dichloromethane/methanol 10:1 Rf=0.15). ES+ MS m/e 397 (MH+).
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