Tetrahydrofuran → N-[[(5S)-3-[3-Fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Participants

Reaction Steps

Phenylmethyl [3-fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]carbamate (1.70 g, 4.07 mmol) is dissolved in dry THF (18 ml) under nitrogen and cooled to −78°. A 1.6 M solution of n-butyl lithium (2.7 ml, 4.32 mmol) in hexane is added and stirred for 1 hr. A solution of N-[(2S)oxiranylmethyl]acetamide 11 (960 mg, 8.35 mmol) in dry THF (6.5 ml) is added and the stirred mixture allowed to come to 25° overnight. Solvent is evaporated and the residue partitioned between chloroform (100 ml) and ammonium chloride solution (50 ml). The organic layer is washed with brine (40 ml), dried (MgSO4) and evaporated. The residue is chromatographed over silica gel (150 g) eluting with 2-4% methanol-chloroform to afford the oxazolidinone as a white foam (1.275 g, 73%). HRMS(FAB) calcd for m+H=426.1499: Found; 426.1506.

Provenance & Evidence