Hydrochloric Acid → HCID 42633438, compound

Participants

Reaction Steps

Ethyl 4-benzyl-7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (36 mg, 0.096 mmol), glycine (145 mg, 1.93 mmol), sodium ethoxide (98 mg, 1.44 mmol) in 3 mL of DMF were refluxed for 2 h. After cooling to room temperature, water (15 mL) and EtOAc (20 mL) were added. The mixture was acidified to pH 2 by addition of 4M hydrochloric acid. The aqueous layer was extracted with additional EtOAc and the combined organic layer was dried over MgSO4. After evaporation of solvent, the residue was redissolved in EtOAc and washed several times with water to remove residual DMF. Drying over MgSO4 followed by evaporation afforded 28 mg of crude solid. The solid was dissolved in 50 mL of saturated sodium bicarbonate solution and washed with hexanes and EtOAc. The aqueous layer was acidified to pH 2 with 4M hydrochloric acid and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 26 mg of the title compound. MS: (+) m/z 404.33 (M+1).

Provenance & Evidence