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

2-Chloro-4-nitro-1H-imidazole (600 g, 4.07 mol) and (R)-2-methyloxiran-2-ylmethyl 4-nitrobenzoate (1060 g, 4.47 mol) were dissolved in ethyl acetate (2124 ml), triethylamine (113.64 ml, 0.82 mol) was added to the solution, and the resulting mixture was stirred under reflux for 16 hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate (530 ml) and toluene (5300 ml) were added to the residue. The resulting precipitates were filtered off and dissolved in methanol (10.6 1). Potassium carbonate (55.4 g, 0.4 mol) was added to the solution, the resulting mixture was stirred at room temperature for 1 hour, concentrated hydrochloric acid (66 ml) and magnesium sulfate (671 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, and the filtrate was concentrated under reduced pressure. To the residue, ethyl acetate (530 ml) and toluene (5300 ml) were added. The resulting precipitates were filtered off and dried at 50° C. to afford (R)-2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole (879.1 g, yield 92%) as a light brown powder.

1. temperatureunder reflux for 16 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate (530 ml) and toluene (5300 ml)
3. additionwere added to the residue
4. customThe resulting precipitates
5. filtrationwere filtered off
6. dissolutiondissolved in methanol (10.6 1)
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
11. concentrationthe filtrate was concentrated under reduced pressure
12. additionTo the residue, ethyl acetate (530 ml) and toluene (5300 ml) were added
13. customThe resulting precipitates
14. filtrationwere filtered off
15. customdried at 50° C.

ORD-Eintrag

ord-3eca78db7bf94f399b0d6454877df6b7

Quelldatensatz

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07262212B2