Thionyl Chloride → HCID 51352133, compound

Participants

Reaction Steps

1-{4′-[4-(2,2-Difluoro-4-phenyl-butyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid (0.225 g, 0.441 mmol) was dissolved in CH2Cl2 (2.3 mL) and thionyl chloride (0.07 mL, 0.971 mmol) was added. After 30 minutes the reaction was concentrated. Separately, methanesulfonamide (0.124 g, 1.30 mmol) was dissolved in THF (2 mL) and sodium hydride (60% in mineral oil, 0.044 g, 1.103 mmol) was added. The acid chloride from the first reaction was dissolved in THF and carefully added to the second mixture. The reaction was monitored by analytical LCMS and excess sodium hydride was added until the reaction went to completion. Standard aqueous workup and silica gel chromatography (0-100% EtOAc in hexanes) afforded the title compound.

Provenance & Evidence