Hydrochloric Acid → HCID 42633442, compound

Participants

Reaction Steps

3-Ethyl-7-hydroxy-isoxazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (80 mg, 0.42 mmol) was dissolved in 12 mL of DMF. Glycine (0.51 g, 6.78 mmol) and sodium ethoxide (0.35 g, 5.08 mmol) were added and the mixture was refluxed for 2 h. The mixture was cooled to room temperature and diluted with 60 mL of water. EtOAc (50 mL) was added and the resulting biphasic mixture was stirred vigorously as 4M hydrochloric acid was added dropwise until pH was 3. The aqueous layer was extracted with additional EtOAc, and the combined organic layer was washed with water and dried over MgSO4. The solvent was evaporated and the solid residue was taken up in 50 mL of saturated sodium bicarbonate solution. The aqueous phase was washed with hexanes and EtOAc. The aqueous layer was then acidified to pH 2 by addition of concentrated hydrochloric acid and extracted with EtOAc (3×50 mL). The combined organic layer was dried over MgSO4 and concentrated to give 56 mg of the title compound. MS: (+) m/z 266.32 (M+1).

Provenance & Evidence