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

HRID 856203Notes

Reaction equation

HRID 856203 reaction equation
[F:1][C:2]([F:34])([F:33])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C@@:20]([OH:32])([CH3:31])[CH2:21][N:22]3[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[N:24]=[C:23]3Cl)=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]([F:34])([F:33])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C@:20]3([CH3:31])[O:32][C:23]4=[N:24][C:25]([N+:27]([O-:29])=[O:28])=[CH:26][N:22]4[CH2:21]3)=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69479536(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethoxyphenyl)piperazine-1-carboxylate

Product 1

HCID 69481138(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethoxyphenyl)piperazine-1-carboxylateYield 59.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethoxyphenyl)piperazine-1-carboxylate prepared in Example 93 (1.29 g, 2.5 mmol) in DMF (13 ml), sodium hydride (0.12 g, 3 mmol) was added followed by stirring for 1 hour with cooling on ice-bath. To the reaction mixture, ice water was added, and the precipitates were filtered off, washed with water and recrystallized from isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethoxyphenyl)piperazine-1-carboxylate (0.70 g, yield 59%) as a white solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. filtrationthe precipitates were filtered off
  3. washwashed with water
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-41165795bdf24676ae5e94bb46660605
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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