Sodium Azide → (5R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxazolidinone

Participants

Reaction Conditions

Reaction Steps

The [[3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-p-toluenesulfonate (2.0 g, 4.287 mmol) was dissolved in dry DMF (15 mL) and then treated with solid NaN3 (1.67 g, 25.722 mmol). The reaction was heated to 65° C. (external temperature) for 6 hours, after which the reaction was allowed to cool to ambient temperature, stirring over a long weekend (158 hours). At this point, the reaction was found to be complete by TLC (6% CH3CN/CHCl3, UV short wave). The reaction was diluted with EtOAc (300 mL) and then washed with water (3×250 mL). The aqueous portions were back-extracted with more EtOAc (2×150 mL). The EtOAc portions were combined, dried over Na2SO4, filtered and concentrated under reduced pressure to give 1.447 g (100%) of the title compound as an off-white solid with a melting point of 91.5°-93° C. and a HRMS (M+) calculated for C14H16N5O5FS 337.1009, found 337.1009.

Provenance & Evidence