Reaktion #439206

Reaktionsgleichung

2-acetoxymethoxy-1,3-diacetoxypropane

2-Nitroimidazole

1-[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl-2-nitroimidazole

dibutyl tin oxide

sodium phosphate

ammonia

1-[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl-2-nitroimidazole

hexamethyldisilazane

→

1-[1-acetoxymethyl-2-(hydroxy)ethoxy]methyl-2-nitroimidazole

Lösungsmittel

acetonitrile

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under reduced pressure, and anhydrous methylene chloride (16 mL) and anhydrous tetrahydrofuran (4 mL)
2. 2
   workup.ADDITIONwere added to the residue
3. 3
   workup.ADDITIONacetyl chloride (171 mg) was added to the mixture
4. 4
   SonstigeTo the resultant reaction mixture
5. 5
   workup.ADDITIONwas added
6. 6
   Filtrationthe resultant mixture was subjected to filtration
7. 7
   ExtraktionThe resultant residue was subjected to extraction with chloroform (10 mL×3)
8. 8
   Extraktionthe thus-obtained extract
9. 9
   workup.ADDITIONwas mixed with the filtrate
10. 10
    Sonstigethe mixture was separated
11. 11
    Sonstigeobtaining an organic layer
12. 12
    TrocknenThe organic layer was dried over sodium sulfate
13. 13
    Sonstigepurified through silica gel chromatography

Vorschrift

2-Nitroimidazole was subjected to trimethylsilylation by use of hexamethyldisilazane in acetonitrile, and the resultant compound and 2-acetoxymethoxy-1,3-diacetoxypropane were subjected to condensation by use of stannic chloride serving as a catalyst. The resultant product was deprotected by use of methanolic ammonia, to thereby obtain 1-[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl-2-nitroimidazole. The thus-obtained 1-[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl-2-nitroimidazole (0.5 g) was refluxed for two hours together with dibutyl tin oxide (0.6 g) in anhydrous toluene in the presence of molecular sieves having a pore size of 4 Å. The solvent was removed under reduced pressure, and anhydrous methylene chloride (16 mL) and anhydrous tetrahydrofuran (4 mL) were added to the residue. The resultant mixture was cooled to 0° C., and acetyl chloride (171 mg) was added to the mixture, and then the mixture was stirred for 30 minutes. To the resultant reaction mixture, a sodium phosphate buffer having a pH of 7.1 (10 mL) was added, and the resultant mixture was subjected to filtration. The resultant residue was subjected to extraction with chloroform (10 mL×3), and the thus-obtained extract was mixed with the filtrate, and the mixture was separated, thereby obtaining an organic layer. The organic layer was dried over sodium sulfate, and then fractionated and purified through silica gel chromatography, to thereby yield the title compound, 1-[1-acetoxymethyl-2-(hydroxy)ethoxy]methyl-2-nitroimidazole (265 mg).

Quelle