Hydrochloric Acid → (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl N-(4-chlorophenyl)-N-methylcarbamate

HRID 856187Notes

Reaction equation

HRID 856187 reaction equation
I[CH3:2].[OH-].[K+].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:29])[O:14][CH2:15][C@@:16]([OH:28])([CH3:27])[CH2:17][N:18]2[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[N:20]=[C:19]2Cl)=[CH:8][CH:7]=1.Cl>CS(C)=O>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH3:2])[C:13](=[O:29])[O:14][CH2:15][C@:16]2([CH3:27])[O:28][C:19]3=[N:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][N:18]3[CH2:17]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 69481886(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-chlorophenylcarbamate

Product 1

HCID 69481938(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl N-(4-chlorophenyl)-N-methylcarbamateYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Iodomethane (0.71 ml, 11.4 mmol) and potassium hydroxide (0.64 g, 11.4 mmol) were added to a solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-chlorophenylcarbamate prepared in Example 64 (1.5 g, 3.8 mmol) in DMSO (40 ml) followed by stirring at room temperature for 4 hours. The mixture was cooled on ice-bath and added 10% hydrochloric acid. The resulting mixture was extracted with ethyl acetate, and 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 (n-hexane/ethyl acetate=1/1) and recrystallized from isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl N-(4-chlorophenyl)-N-methylcarbamate (0.67 g, 60%) as a white solid.

Workup

  1. temperatureThe mixture was cooled on ice-bath
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-4437f7db2a4d4ff9a4ad01db8a9346eb
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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