Hydrochloric Acid → {[4-Cyano-7-hydroxy-3-(4-methoxy-phenyl)-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid

Participants

Reaction Steps

Ethyl 4-cyano-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate (86 mg, 0.254 mmol) and glycine (381 mg, 5.07 mmol) were added to sodium methoxide solution (7.6 mL, 3.80 mmol, 0.5 M in MeOH) and the mixture was refluxed for 3 days. The mixture was cooled to room temperature and 0.25 M hydrochloric acid was added until pH was 3. The precipitate was isolated by filtration and dried under vacuum to give 75 mg of crude solid. The solid was dissolved in 200 mL of saturated sodium bicarbonate solution and washed with EtOAc. The aqueous layer was acidified to pH 3 with concentrated hydrochloric acid and the precipitate was collected by filtration. The solid was dried under vacuum to afford 67 mg of the title compound. MS: (−) m/z 367.34 (M−1).

Provenance & Evidence