[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[C:5]([CH3:13])=[N:6][C:7]=1[C:8](OCC)=[O:9].[NH2:23][CH2:24][C:25]([OH:27])=[O:26].[O-]CC.[Na+].Cl>CN(C=O)C.O>[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:4]=2[C:5]([CH3:13])=[N:6][C:7]=1[C:8]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:9]
Ethyl 7-hydroxy-4-methyl-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (41 mg, 0.138 mmol) was dissolved in 5 mL of DMF. Glycine (207 mg, 2.75 mmol) and sodium ethoxide (140 mg, 2.06 mmol) were added and the mixture was refluxed for 2 h. The mixture was cooled to room temperature and diluted with 30 mL of water. Concentrated hydrochloric acid was added dropwise until pH was 3. The aqueous phase was extracted with EtOAc and the combined organic layer was dried over MgSO4 and concentrated to give 35 mg of pale yellow solid. The solid was dissolved in saturated NaHCO3 (10 mL) and washed with hexanes and EtOAc. The aqueous phase was acidified to pH 3 with concentrated HCl and extracted with EtOAc. The organic layer was dried and concentrated to give 15 mg of the title compound. MS: (+) m/z 328.39 (M+1).
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