[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([O:10]CC)=O.[NH2:22][CH2:23][C:24]([OH:26])=[O:25].[O-]CC.[Na+].Cl>CN(C=O)C.O.CCOC(C)=O>[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:10]Ethyl 7-hydroxy-3-(pyridin-4-yl)isoxazolo[4,5-c]pyridine-6-carboxylate (95 mg, 0.33 mmol) was dissolved in 10 mL of DMF. Glycine (500 mg, 6.67 mmol) and sodium ethoxide (340 mg, 5.0 mmol) were added and the mixture was refluxed for 2 h. The mixture was cooled to room temperature and diluted with 50 mL of water. Concentrated hydrochloric acid was added dropwise until pH was 3. EtOAc (50 mL) was added to the resulting suspension, and the mixture was transferred to a separatory funnel. The aqueous layer was removed, and the organic layer, which contained an insoluble solid, was filtered. The solid was dried under vacuum to give 30 mg of the title compound. MS: (+) m/z 315.34 (M+1).
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