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

HRID 856187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 856187
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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4437f7db2a4d4ff9a4ad01db8a9346eb
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262212B2

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