Hydrochloric Acid → HCID 42633439, compound

Participants

Reaction Steps

Ethyl 4-(1-benzyl-1H-1,2,3-triazol-4-yl)-7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (100 mg, 0.227 mmol), glycine (340 mg, 4.54 mmol) and sodium ethoxide (231 mg, 3.40 mmol) were added to 8 mL of DMF and the mixture was refluxed for 2 h. After the mixture was cooled to room temperature, water (50 mL) and EtOAc (50 mL) were added. The biphasic 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 and concentrated to give an oily residue. The residue was dissolved in 300 mL of saturated sodium bicarbonate solution and washed with hexanes EtOAc. The aqueous layer was acidified with concentrated hydrochloric acid to pH 2 and extracted with EtOAc. The solvent was concentrated in vacuo to give 91 mg of the title compound. MS: (+) m/z 471.29 (M+1).

Provenance & Evidence