反应详情

117 mg of the thus-obtained 1-[1-acetoxymethyl-2-(hydroxy)ethoxy]methyl-2-nitroimidazole was placed in a flask together with dry pyridine, and 252 mg of toluenesulfonyl chloride was added. The mixture was stirred for 5 hours at room temperature. The reaction mixture was extracted with 30 ml of added ethyl acetate, and the obtained extract was subjected to partition and water washing, two times with 30 ml of water. The organic phase was dried over sodium sulfate, subsequently concentrated under reduced pressure, and purified by silica gel column chromatography, to obtain 1-[1-acetoxymethyl-2-mesylethoxy]methyl-2-nitroimidazole. 10 ml of dry DMF was added to dissolve the product, and the solution was added to a mixture which had been prepared by mixing 10 ml of acetonitrile and 1 ml of water in advance, adding 33.8 mg of potassium fluoride and 80 mg of 18-crown-6, and drying under reduced pressure. The resulting mixture was heated at 110° C. for 8 hours. To the obtained reaction mixture, 20 ml of ethyl acetate was added, and the mixture was washed with 20 ml of water. The aqueous phase was extracted two times with 20 ml of ethyl acetate, and the obtained extract was combined with the organic phase and dried to solid under reduced pressure. The dried product was purified by preparative high performance chromatography, to obtain 15.4 mg of 1-(1-hydroxymethyl-2-fluoro)ethoxymethyl-2-nitroimidazole. From the mass analysis results for this product, M+1(219) was recognized, and thus the structure was confirmed. Also, the elemental analysis values resulted in 38.55% of carbon, 4.11% of hydrogen, 19.28% of nitrogen, and 8.70% of fluorine, thus supporting the structure.

1. additionwas added
2. extractionThe reaction mixture was extracted with 30 ml of added ethyl acetate
3. extractionthe obtained extract
4. customto partition
5. dry with materialThe organic phase was dried over sodium sulfate
6. concentrationsubsequently concentrated under reduced pressure
7. custompurified by silica gel column chromatography