Bromoacetonitrile → HCID 10429088, compound

Participants

Reaction Steps

(5R)-3-[3-Fluoro-4-(1H-1,2,3-triazol4-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 7, 1.5 g, 4.6 mmol) was stirred in N,N-dimethylformamide at 0° C. Sodium hydride (0.35 g, 9.2 mmol) was added and the mixture was stirred 30 minutes. Bromoacetonitrile (0.66 g, 5.5 mmol) was added and the reaction was stirred overnight, slowly warming to room temperature. Starting material was present so additional bromoacetonitrile (0.33 g, 2.8 mmol) was added and the reaction was stirred for two additional days. The mixture was diluted with water and extracted using ethyl acetate. The organic layer was washed with water, dried (magnesium sulfate) and concentrated under vacuum to give a yellow solid (1.84 g). The solid was dissolved in dimethylsulfoxide (18 ml) and water (5 ml) and the isomers were separated using Gilson HPLC. Peaks 1 and 2 were collected, concentrated and lyophilized to give a light yellow solid (Example 10, peak 1, 36 mg; Example 11, peak 2, 182 mg). NOE experiments were used to distinguish the two isomers with the cyano group of peaks 1 and 2 corresponding to the 1 and 2 positions of the nitrogen, respectively.

Provenance & Evidence