[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[CH2:18][C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=3)=O)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:4].Cl.[NH2:36][OH:37].C(=O)([O-])O.[Na+].[NH4+].[Cl-]>C(O)C.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([CH:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[CH2:18][C:19](=[N:36][OH:37])[C:21]3[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=3)=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)=[O:4]A solution of 4′-[3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester (36 mg), hydroxylamine hydrochloride (11 mg) and sodium hydrogencarbonate (14 mg) in a mixture of ethanol (0.5 mL) and water (0.1 mL) was heated under reflux for 1.5 hours. A saturated solution of NH4Cl was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 2:1) to yield the title compound as a mixture of E and Z isomers (3.3:1) as a white foam (28 mg, 75%), MS (ESI+): m/z=465.2 ([M+H]+).
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