Hydrochloric Acid → HCID 42633441, compound

Participants

Reaction Steps

3-Cyclohex-1-enyl-7-hydroxy-isoxazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (77 mg, 0.27 mmol) was dissolved in 10 mL of DMF. Glycine (0.40 g, 5.35 mmol) and sodium ethoxide (0.27 g, 4.01 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 the resulting precipitate was isolated by filtration to give 65 mg of the title compound. MS: (+) m/z 318.26 (M+1).

Provenance & Evidence