Hydrochloric Acid → (2R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methyl-1,2-propanediol

2-Chloro-4-nitro-1H-imidazole (6.78 g, 46 mmol) and 2-methyloxiran-2-ylmethyl 4-nitrobenzoate (12 g, 51 mmol) were dissolved in ethyl acetate (24 ml), and triethylamine (1.3 ml, 9.2 mmol) was added to the solution. The resulting mixture was stirred under reflux for 14 hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride (40 ml) was added to the residue. The resulting precipitates were filtered off, and dissolved in methanol (120 ml). To the solution, potassium carbonate (318 mg, 2.3 mmol) was added, and the resulting mixture was stirred at room temperature for 1 hour. To the resulting mixture, 6 N hydrochloric acid (0.8 ml) and magnesium sulfate (8 g) were added in this order with cooling on ice-bath, and the resulting mixture was stirred for 30 minutes. Insoluble matters were removed by filtration through Celite, and the filtrate was concentrated under reduced pressure. To the residue, ethyl acetate (6 ml) and toluene (60 ml) were added. The resulting precipitates were filtered off and dried at 50° C. to afford 2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole (7.88 g, yield 72%) as a white powder.

1. temperatureunder reflux for 14 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride (40 ml)
3. additionwas added to the residue
4. customThe resulting precipitates
5. filtrationwere filtered off
6. dissolutiondissolved in methanol (120 ml)
7. stirringthe resulting mixture was stirred at room temperature for 1 hour
8. temperaturewith cooling on ice-bath
9. stirringthe resulting mixture was stirred for 30 minutes
10. customInsoluble matters were removed by filtration through Celite
11. concentrationthe filtrate was concentrated under reduced pressure
12. additionTo the residue, ethyl acetate (6 ml) and toluene (60 ml) were added
13. customThe resulting precipitates
14. filtrationwere filtered off
15. customdried at 50° C.

ORDレコード

ord-323b1834235348d6ab42ac675a06f6fd

出典データセット

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07262212B2