To a mixture of O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (73.8 mg, 0.63 mmol), HOBT (340 mg, 2.5 mmol), NaHCO3 (423 mg, 2.9 mmol), and the (S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hexanoic acid in 30 mL DCM was added EDC.HCl (407 mg, 2.1 mmol) as solid. The reaction mixture was stirred for 3 h at room temperature and then the solvent was removed under reduced pressure. The product was isolated by flash column chromatography, eluting with 10% to 60% EtOAc/Hexane gradient solvent to give 128 mg of the title compound.
