Sodium Bicarbonate → tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylate

Participants

Reaction Steps

To the solution of 2-Chloro-4-nitro-1H-imidazole (89.4 g, 606 mmol) and tert-butyl (S)-4-(2-methyloxiran-2-ylmethyl)piperazine-1-carboxylate (119 g, 466 mmol) in ethanol (475 ml), sodium hydrogen-carbonate (58.7 g, 699 mmol) was added followed by stirring under reflux for 6 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added water. The mixture was extracted with ethyl acetate, and the extract was dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was dispersed into ethyl acetate, and filtered off to afford a solid. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (n-hexane/acetone=3/1) to afford a solid. The solids were combined and dried under reduced pressure to afford tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylate (84.7 g, yield 45%) as a white powder.

Provenance & Evidence