Heptanoyl chloride → (4S)-4-Benzyl-3-heptanoyl-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

n-Butyl lithium (58 mL, 2.5M in hexanes, 142 mmol) is added to a solution of (S)-4-benzyl-2-oxazolidinone 51 (25 g, 141 mmol) in THF (250 mL) at -78° C. under argon and stirred for 15 min. Heptanoyl chloride 50 (21 g, 141 mmol) is added to the solution dropwise and stirred for 40 min, then warmed to 0° C. for 2 hours. The reaction is quenched with NH4Cl and extracted with EtOAc. The organic layer is washed with 1N HCl, aqueous NaHCO3, aqueous NACl, and dried over MgSO4. The crude product is recrystallized from hexane to give 52.

Provenance & Evidence