m-Chloroperbenzoic acid → HCID 58577841, compound
Reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][C:13]([CH3:45])([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:34]=[C:33]3[C:28]([C:29]([C:36](=[O:44])[NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:30][C:31]([CH3:35])=[N:32]3)=[CH:27][CH:26]=2)=[CH:21][N:20]=1)[C:14]([OH:16])=[O:15]>C(Cl)Cl>[C:14]([C:13]([CH3:45])([CH3:12])[CH2:17][O:18][C:19]1[N:20]=[CH:21][C:22]([C:25]2[CH:34]=[C:33]3[C:28]([C:29]([C:36](=[O:44])[NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:30][C:31]([CH3:35])=[N+:32]3[O-:6])=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)([OH:16])=[O:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
m-Chloroperoxybenzoic acid (30.0 mg, 0.20 mmol) was added at room temperature to a solution of 2,2-dimethyl-3-(5-(2-methyl-4-(phenylcarbamoyl)quinolin-7-yl)pyridin-2-yloxy)propanoic acid B-17 (45.5 mg, 0.10 mmol) in methylene chloride (7 mL). The reaction mixture was stirred at room temperature overnight, then concentrated to dryness under reduced pressure. The residue was purified by flash column chromatography on C18 reverse phase (water:acetonitrile gradient with 0.05% formic acid) to give 7-(6-(2-carboxy-2-methylpropoxy)pyridin-3-yl)-2-methyl-4-(phenylcarbamoyl)quinoline 1-oxide B-23 (16.0 mg, Yield=40%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.28 (s, 6H), 2.66 (s, 3H), 4.34 (s, 2H), 7.17 (d, J=6.0 Hz, 1H), 7.40-7.46 (m, 3H), 7.80 (d, J=8.0 Hz, 2H), 7.93 (d, J=8.5 Hz, 1H), 7.99 (s, 1H), 8.14 (d, J=8.5 Hz, 1H), 8.41 (d, J=8.5 Hz, 1H), 8.83 (s, 1H), 8.87 (s, 1H), 10.78 (s, 1H). MS (ESI) [M+1]+ 474.