CO[C:3]([C:5]1[N:10]=[CH:9][C:8]2[N:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][C:7]=2[C:6]=1[OH:20])=[O:4].[NH2:21][CH2:22][C:23]([OH:25])=[O:24]>C[O-].[Na+].CO>[OH:20][C:6]1[C:7]2[O:13][C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:11][C:8]=2[CH:9]=[N:10][C:5]=1[C:3]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:4]7-Hydroxy-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (100 mg, 0.37 mmol), and glycine (583 mg, 7.77 mmol) were suspended in 14.8 mL of 0.5N sodium methoxide in methanol. The reaction mixture was heated at reflux temperature overnight, then cooled, and concentrated. The residue was dissolved in water (30 mL), and the solution was acidified to pH 1-2 with 2N HCl, and subsequently extracted with ethyl acetate. The combined organic layers were dried, and concentrated to produce 104 mg of the title compound as a yellow solid. MS: (+) m/z 314.0 (M+1).
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