Potassium Carbonate → 3-[(5,5-dioxido-3,4-dihydro-2H-1,5-benzoxathiepin-8-yl)oxy]-5-{[(s)-1-methyl-2-(methyloxy)ethyl]oxy}benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}benzoic acid (0.245 g, 1.08 mmol), 8-fluoro-3,4-dihydro-2H-1,5-benzoxathiepine 5,5-dioxide (235 mg, 1.08 mmol) and potassium carbonate (299 mg, 2.17 mmol) in acetonitrile (7.8 mL) was heated in a microwave reactor at 160° C. for 5 hours. The mixture was reduced in vacuo and the residue purified by preparative HPLC (on a C18 reversed phase using 5-95% acetonitrile (+0.2% TFA) in water (+0.2% TFA) as eluant) to give the desired compound as a beige solid (222 mg). 1H NMR δ (d6-DMSO): 1.22 (d, 3H), 2.22-2.24 (m, 2H), 3.17 (s, 3H), 3.43-3.58 (m, 4H), 4.03-4.16 (m, 1H), 4.16-4.25 (m, 2H), 4.63-4.73 (m, 1H), 6.80-6.85 (m, 1H) 6.90-7.01 (m, 2H), 7.15 (s, 1H), 7.35 (s, 1H), 7.83 (d, 1H); m/z 421 (M−H)−

Provenance & Evidence