Glycine → HCID 42633246, compound

Participants

Reaction Steps

Ethyl 7-hydroxy-3-phenyl-4-((trimethylsilyl)ethynyl)isoxazolo[4,5-c]pyridine-6-carboxylate (200 mg, 0.53 mmol) was added to sodium methoxide solution (39.5 mL, 19.7 mmol, 0.5 M in MeOH) and the mixture was refluxed for 30 min. After the mixture was cooled to room temperature, glycine (1.98 g, 26.3 mmol) was added, and the mixture was refluxed for 48 h. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in 100 mL of water and hydrochloric acid was added until pH was 3. The precipitate was isolated by filtration and dried under vacuum to give 170 mg of crude solid. The solid was dissolved in 100 mL of saturated sodium bicarbonate solution and washed with EtOAc. The aqueous layer was acidified with concentrated hydrochloric acid to pH 3 and extracted with EtOAc. The solvent was concentrated in vacuo to give 116 mg of the title compound. MS: (−) m/z 336.28 (M−1).

Provenance & Evidence