Sodium hydride → 2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethoxyphenyl)piperazine-1-carboxylate

Sodium hydride (23 mg, 0.56 mmol) was added to a solution of 3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethoxyphenyl)piperazine-1-carboxylate prepared in Example 83 (0.24 g, 0.47 mmol) in DMF (2 ml) followed by stirring at 0° C. for 1 hour. Ice-water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and then washed with diisopropyl ether to afford 2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethoxyphenyl)piperazine-1-carboxylate (0.13 g, yield 58%) as a white solid.

1. extractionthe resulting mixture was extracted with ethyl acetate
2. washThe extract was washed with water
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
6. washwashed with diisopropyl ether

ORD record

ord-747abad93b5a47d38e579fa2c7e34ea4

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262212B2