Hydrochloric Acid → (betaR)-2-Chloro-beta-hydroxy-beta-methyl-4-nitro-1H-imidazole-1-propanol 1-Methanesulfonate

HRID 856152Notes

Reaction equation

HRID 856152 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][C@:11]([OH:15])([CH3:14])[CH2:12][OH:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]([CH2:10][C@:11]([OH:15])([CH3:14])[CH2:12][O:13][S:17]([CH3:16])(=[O:19])=[O:18])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 16099121(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methylpropane-1,2-diol

Product 1

HCID 16099134(betaR)-2-Chloro-beta-hydroxy-beta-methyl-4-nitro-1H-imidazole-1-propanol 1-MethanesulfonateYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

(R)-2-Chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole prepared in Example 10 (879 g, 3.73 mol) was dissolved in pyridine (1778 ml) and cooled to 5° C. To this solution, methanesulfonyl chloride (432.7 ml, 5.59 mol) was added dropwise below 15° C., and the resulting mixture was stirred at the same temperature for 1 hour. To the mixture, 6N hydrochloric acid (5500 ml) was added below 30° C., and the resulting mixture was stirred for 40 minutes with cooling on ice-bath. The precipitates were filtered off and washed with water and toluene in this order to afford primary crystals. In addition, the filtrate was extracted with ethyl acetate (5 liters) twice. The organic phase was washed with water, dried over magnesium sulfate, and filtered to afford a solid. The filtrate was concentrated under reduced pressure. To the residue, toluene was added and the precipitates were filtered off to afford a solid. The solids were combined and dried at 60° C. to afford (R)-2-chloro-1-(2-hydroxy-3-methanesulfonyloxy-2-methylpropyl)-4-nitroimidazole (942.6 g, yield 81%) as a white powder.

Workup

  1. stirringthe resulting mixture was stirred for 40 minutes
  2. temperaturewith cooling on ice-bath
  3. filtrationThe precipitates were filtered off
  4. washwashed with water and toluene in this order
  5. customto afford primary crystals
  6. extractionIn addition, the filtrate was extracted with ethyl acetate (5 liters) twice
  7. washThe organic phase was washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customto afford a solid
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. additionTo the residue, toluene was added
  13. filtrationthe precipitates were filtered off
  14. customto afford a solid
  15. customdried at 60° C.

Sources & evidence

ORD record
ord-cbc1b3202f4b4f7dbaf407433013591c
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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