1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole

(R)-2-Chloro-1-(2-hydroxy-3-methanesulfonyloxy-2-methylpropyl)-4-nitroimidazole prepared in Example 11 (942.6 g, 3 mol) was suspended in ethyl acetate (9426 ml). DBU (494 ml, 3.3 mol) was added to the suspension, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was washed with water (5 liters). The water layer was extracted with ethyl acetate (5 liters) twice. The organic phases were combined together, and the mixture was washed with a saturated saline solution (5 liters), dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2) to afford (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole (600.7 g, yield 92%) as a white powder.

1. washThe reaction mixture was washed with water (5 liters)
2. extractionThe water layer was extracted with ethyl acetate (5 liters) twice
3. washthe mixture was washed with a saturated saline solution (5 liters)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2)

ORD record

ord-3279f2fba7564b58948c1dce15630afd

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262212B2