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

HRID 856191Notes

Reaction equation

[H-].[Na+].[F:3][C:4]([F:36])([F:35])[O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]([OH:34])([CH3:33])[CH2:23][N:24]3[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[N:26]=[C:25]3Cl)=[O:19])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1>CN(C=O)C>[F:3][C:4]([F:36])([F:35])[O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3([CH3:33])[O:34][C:25]4=[N:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][N:24]4[CH2:23]3)=[O:19])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-747abad93b5a47d38e579fa2c7e34ea4
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262212B2

Reaction notes

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