Carbon Dioxide → HCID 449162, compound

Participants

Reaction Steps

To a solution of ethyl 4-((acetyloxy)methyl)-5-(3-{(1E)-3-(3-hydroxy-2-(methoxycarbonyl)phenoxy)prop-1-enyl}phenyl)isoxazole-3-carboxylate (190 mg, 0.38 mmol) in EtOH (1.5 mL) was added 1 mL THF and 3 mL aqueous K2CO3 (sat'd). After 1.5 hour at ambient temperature 4 M HCl was added until CO2 evolution ceased. A precipitate formed which was filtered and dissolved in DMSO for purification by reverse phase HPLC (0–70% acetonitrile in 0.1% aqueous TFA) to provide the titled compound (100 mg, 61%). 1H NMR (300 MHz, DMSO-d6) δ 9.98 (s, 1H), 7.94 (broad s, 1H), 7.77 (broad d, J=7.8 Hz, 1H), 7.69 (broad d, J=7.8 Hz, 1H), 7.58 (t, J=7.8 Hz, 1H), 7.19 (t, J=8.3 Hz, 1H), 6.81 (broad d, J=16 Hz, 1H), 6.60 (d, J=8.3 Hz, 1H), 6.57 (dt, J=16, 5.2 Hz, 1H), 6.51 (d, J=8.3 Hz, 1H), 4.75 (d, J=5.2 Hz, 2H), 4.65 (s, 2H), 3.78 (s, 3H). MS (ESI+) m/z 426 (M+H)+, 443 (M+NH4)+, 448 (M+Na)+: (ESI−) m/z 424 (M−H)−, 380 (M−CO2H)−.

Provenance & Evidence