Sodium hydride → HCID 69481215, compound

HRID 856205Notes

Reaction equation

HRID 856205 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:33]=[CH:32][C:6]([CH:7]=[N:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C@@:19]([OH:31])([CH3:30])[CH2:20][N:21]3[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[N:23]=[C:22]3Cl)=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[Na+]>CN(C=O)C>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:33]=[CH:32][C:6]([CH:7]=[N:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C@:19]3([CH3:30])[O:31][C:22]4=[N:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][N:21]4[CH2:20]3)=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69481807HCID 69481807, compound

Product 1

HCID 69481215HCID 69481215, compoundYield 69.4%

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-trifluoromethylbenzylideneamino)piperazine-1-carboxylate prepared in Example 103 (4.03 g, 7.77 mmol) in DMF (20 ml), sodium hydride (0.37 g, 9.32 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 acetonitrile-isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-trifluoromethylbenzylideneamino)piperazine-1-carboxylate (2.60 g, yield 69%) as a white solid. Melting point 176-178° C.

Workup

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

Sources & evidence

ORD record
ord-efbe67cca694418896e832f32314909f
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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