Water → ((3S)-6-[(2,4-Difluorobenzyl)oxy]-2,3-dihydro-1-benzofuran-3-yl)acetic acid

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Reaction Conditions

Reaction Steps

To a stirred mixture of methyl(3S)-(2,3-dihydro-6-hydroxy-1-benzofuran-3-yl)acetate (20.8 mg) and K2CO3 (20.7 mg) in DMF (0.5 mL) was added 2,4-difluorobenzyl chloride (24.4 mg) at room temperature. After stirring at 55° C. for 15 h, water (2.0 mL) and EtOAc (3.0 mL) were added to the mixture with stirring. The organic layer was separated by phase separation filter kit, and the filtrate was evaporated by blowing away with the air at 60° C. The resulting residue was dissolved in MeOH (0.5 mL) and 1N LiOH (0.3 mL), and the mixture was stirred at room temperature for 1 h. To the mixture was added 1N HCl (0.2 mL) and the solution was evaporated by blowing away with the air at 60° C. The resulting residue was dissolved in DMSO (1.0 mL) and the solution was purified by preparative HPLC (C18, eluent: water/CH3CN (including 5 mM AcONH4)). The eluted fraction was evaporated by air blowing at 60° C. to give the title compound (11.0 mg, 34.4%).

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