Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:8]([O:10][CH3:11])=[O:9])=O.[C:16]([O-:19])([O-])=O.[K+].[K+].Cl.OCC[CH2:26][C:27](=[NH:30])OC.C[N:32](C)C=O>>[OH:19][CH2:16][CH2:26][C:27]1[NH:30][C:3]([C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=2[CH3:15])[C:8]([O:10][CH3:11])=[O:9])=[CH:2][N:32]=1Into a 250-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 3-(2-bromoacetyl)-4-methylbenzoate (compound 27.2, 10 g, 36.89 mmol) in N,N-dimethylformamide (150 mL). K2CO3 (30 g, 215.5 mmol) and 3-hydroxypropanimidamide hydrochloride (compound 23.1, 15 g, 120.4 mmol) were added to the reaction. The reaction mixture was stirred for 12 h at 80° C., then concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (2:1) as eluent to furnish 2 g (21%) of the title compound as a light yellow oil.
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