Ethyl Acetate → HCID 9976903, compound

HRID 856306Notes

Reaction equation

HRID 856306 reaction equation
Cl[C:2]1[N:3]([CH2:10][C@@:11]([CH3:27])([OH:26])[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+].C(OCC)(=O)C>CN(C=O)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([N:16]2[CH2:17][CH2:18][N:13]([CH2:12][C@:11]3([CH3:27])[O:26][C:2]4=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]4[CH2:10]3)[CH2:14][CH2:15]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 69479382HCID 69479382, compound

Product 1

HCID 9976903HCID 9976903, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-1-(2-Chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-chlorophenyl)piperazin-1-yl]propan-2-ol prepared in Example 370 (33.0 g, 79.7 mmol) was dissolved in DMF (300 ml). To the solution, sodium hydride (3.7 g, 91.6 mmol) was added with cooling on ice-bath followed by stirring at room temperature overnight. To the reaction mixture, ice-water and ethyl acetate were added, and the solution was vigorously stirred. The precipitates were filtered off, washed with water and ethyl acetate, and dried under reduced pressure to afford 23.2 g of a crude light yellow powder. The crude powder was combined with another crude powder synthesized in the same manner (50 g), and the mixture was purified by silica gel column chromatography (methylene chloride/ethyl acetate=50/1) and crystallized from methylene chloride-ethyl acetate to afford (S)-2-[4-(4-chlorophenyl)piperazin-1-ylmethyl]-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (45 g, yield 90%) as a white powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. stirringthe solution was vigorously stirred
  3. filtrationThe precipitates were filtered off
  4. washwashed with water and ethyl acetate
  5. customdried under reduced pressure
  6. customto afford 23.2 g of a crude light yellow powder
  7. customsynthesized in the same manner (50 g)
  8. customthe mixture was purified by silica gel column chromatography (methylene chloride/ethyl acetate=50/1)
  9. customcrystallized from methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-6a3b97d79acf440285457d6bd427dfae
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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