Sodium Bicarbonate → tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylate

HRID 856296Notes

Reaction equation

HRID 856296 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:10][C@:11]1([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:13][O:12]1.C(=O)([O-])O.[Na+]>C(O)C>[Cl:1][C:2]1[N:3]([CH2:13][C@:11]([OH:12])([CH3:10])[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 86604816tert-butyl(S)-4-(2-methyloxiran-2-ylmethyl)piperazine-1-carboxylateHCID 178526855HCID 178526855, compound

Product 1

HCID 69635130tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 2-Chloro-4-nitro-1H-imidazole (89.4 g, 606 mmol) and tert-butyl (S)-4-(2-methyloxiran-2-ylmethyl)piperazine-1-carboxylate (119 g, 466 mmol) in ethanol (475 ml), sodium hydrogen-carbonate (58.7 g, 699 mmol) was added followed by stirring under reflux for 6 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added water. The mixture was extracted with ethyl acetate, and the extract was dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was dispersed into ethyl acetate, and filtered off to afford a solid. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (n-hexane/acetone=3/1) to afford a solid. The solids were combined and dried under reduced pressure to afford tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-piperazine-1-carboxylate (84.7 g, yield 45%) as a white powder.

Workup

  1. temperatureunder reflux for 6 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was added water
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe extract was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. additionThe residue was dispersed into ethyl acetate
  9. filtrationfiltered off
  10. customto afford a solid
  11. concentrationThe filtrate was concentrated
  12. customthe residue was purified by silica gel column chromatography (n-hexane/acetone=3/1)
  13. customto afford a solid
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-122e7acde26d4de6a8a89cd1d4a04781
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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