p-Toluenesulfonic acid monohydrate → HCID 58503962, compound
Reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([CH2:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[O:37][N:36]=[C:35]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:34]=3)[CH2:28][CH2:27]1)[C:18](O)([C:44]([O:46][CH3:47])=[O:45])[CH:17]2[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([CH2:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[O:37][N:36]=[C:35]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:34]=3)[CH2:28][CH2:27]1)[C:18]([C:44]([O:46][CH3:47])=[O:45])=[C:17]2[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
p-Toluenesulfonic acid monohydrate (0.070 g) was added to a suspension of the compound prepared in Example 95 (0.56 g) in toluene (20 mL). The reaction mixture was heated at reflux under Dean-Stark conditions overnight. The reaction mixture was then cooled to room temperature and partitioned between dichloromethane and a saturated aqueous sodium bicarbonate solution. The combined organics were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=3:2) to obtain the title compound (0.35 g) having the following physical data.