Water → 3-(4-trifluoromethylphenyl)-2-propenyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate

HRID 856310Notes

Reaction equation

HRID 856310 reaction equation
Cl[C:2]1[N:3]([CH2:10][C@:11]([OH:36])([CH3:35])[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH:23]=[CH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[O:20])[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+].C(OCC)(=O)C.O>CN(C=O)C>[CH3:35][C@@:11]1([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH:23]=[CH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[O:20])[CH2:15][CH2:14]2)[O:36][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 867605343-(4-trifluoromethylphenyl)-2-propenyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazine-1-carboxylate

Product 1

HCID 866043773-(4-trifluoromethylphenyl)-2-propenyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Trifluoromethylphenyl)-2-propenyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methyl-propyl]piperazine-1-carboxylate prepared in Example 391 (13.2 g, 24.81 mmol) was dissolved in DMF (40 ml). To the solution, sodium hydride (1.19 g, 29.78 mmol) was added followed by stirring for 1.5 hours with cooling on ice-bath. To the reaction mixture, ethyl acetate (13 ml) and water (92 ml) were added in this order followed by stirring for 30 minutes. The precipitates were filtered off, washed with water and purified by silica gel column chromatography (ethyl acetate) to afford 3-(4-trifluoromethylphenyl)-2-propenyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate (10.17 g, yield 83%) as a light yellow powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. stirringby stirring for 30 minutes
  3. filtrationThe precipitates were filtered off
  4. washwashed with water
  5. custompurified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b2a8eb02a16542f58052c96adb114d2c
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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