Hydrochloric Acid → HCID 42633440, compound

Participants

Reaction Steps

Ethyl 7-hydroxy-3-phenyl-4-(trifluoromethyl)isoxazolo[4,5-c]pyridine-6-carboxylate (58 mg, 0.17 mmol), glycine (247 mg, 3.30 mmol), and sodium ethoxide (168 mg, 2.47 mmol) were added to 6 mL of DMF and the mixture was refluxed for 2 h. After the mixture cooled to room temperature, water (50 mL) and EtOAc (50 mL) were added. The mixture was stirred vigorously and 4M hydrochloric acid was added until pH was 3. The aqueous layer was extracted with additional EtOAc and the combined organic layer was dried over MgSO4 and concentrated. The residue was taken up in saturated sodium bicarbonate solution (20 mL) and washed with hexanes and EtOAc. The aqueous layer was acidified to pH 3 with 4M hydrochloric acid and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give a crude solid, which was purified by flash chromatography (0-100% EtOAc/hexanes+2% acetic acid) to give 37 mg of the title compound. MS: (−) m/z 380.19 (M−1).

Provenance & Evidence