Ethyl trifluoromethanesulphonate → (4S,5R)-3-((S)-2-Ethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a −78° C. stirred solution of the (4S,5R)-4-Methyl-3-pentanoyl-5-phenyl-oxazolidin-2-one (9.20 g, 35.2 mmol) in dry THF (150 mL) was added NaHMDS (42.2 mL, 1.0 M in THF) dropwise. After 1 hour, ethyl trifluoromethanesulfonate (5.93 mL, 45.7 mmol) was added dropwise and the reaction was stirred at −78° C. for an additional 2 hours. The reaction was warmed to −30° C. for 30 minutes and quenched with sat. NH4Cl. The layers were separated and the aqueous layer was extracted with EtOAc (3×40 mL). The organic extracts were combined and washed with brine (2×40 mL). The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure to yield 8.05 g of crude product.

Provenance & Evidence