Decanoyl chloride → 2-Oxazolidinone, 3-(1-oxodecyl)-4-(phenylmethyl)-, (4S)-

Participants

Reaction Conditions

Reaction Steps

n-Butyl lithium (160 mL, 398 mmol, 2.5M in hexanes) is added to a solution of (S)-4-benzyl-2-oxazolidinone 51 (64 g, 362 mmol) in THF (750 mL) at -78° C. under argon and stirred for 15 min. Decanoyl chloride 59 (69 g, 362 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 60.

Provenance & Evidence