Water → HCID 42633437, compound

Participants

Reaction Steps

2-(4-ethynyl-7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxamido)acetic acid (60 mg, 0.178 mmol) was dissolved in 6.6 mL of THF. Water (0.7 mL) was added, followed by 1.5 mL of a saturated solution of HgSO4 in 1% H2SO4. The reaction mixture was stirred at room temperature for 16 h. Brine (10 mL) was added and the mixture was extracted with EtOAc. The combined organic layer was dried over MgSO4 and concentrated to give a purple solid. The solid was taken up in 25 mL of saturated sodium bicarbonate solution and washed several times with 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 65 mg of crude solid. The solid was purified by flash chromatography (0-100% EA/hexanes+2% acetic acid) to give 20 mg of the title compound. MS: (−) m/z 354.22 (M−1).

Provenance & Evidence