Triethylamine → HCID 69635341, compound

HRID 856292Notes

Reaction equation

HRID 856292 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][C@@H:11]([OH:24])[CH2:12]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[N:25]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[N:3]([CH2:10][C@@H:11]([OH:24])[CH2:12][N:28]2[CH2:27][CH2:26][N:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86604800HCID 86604800, compound

Product 1

HCID 69635341HCID 69635341, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-2-Chloro-1-[2-hydroxy-3-(4-methylbenzene-sulfonyloxy)propyl]-4-nitroimidazole prepared in Example 8 (16.86 g, 44.86 mmol) and tert-butyl piperazine-1-carboxylate (8.36 g, 44.89 mmol) were dissolved in acetonitrile (100 ml). To the solution, triethylamine (6.3 ml, 45.2 mmol) was added followed by stirring under reflux for 6 hours. The reaction mixture was allowed to return to room temperature, and concentrated under reduced pressure. To the residue, water (100 ml) was added and extracted with ethyl acetate (100 ml) twice. The organic phases were combined, washed with water (100 ml) and a saturated saline solution (100 ml) in this order, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=40/1) and then recrystallized from ethyl acetate/n-hexane to afford tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxypropyl]piperazine-1-carboxylate (11.61 g, yield 66%) as a light yellow powder.

Workup

  1. temperatureunder reflux for 6 hours
  2. customto return to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue, water (100 ml) was added
  5. extractionextracted with ethyl acetate (100 ml) twice
  6. washwashed with water (100 ml)
  7. dry with materiala saturated saline solution (100 ml) in this order, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=40/1)
  11. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-371a129a22834db28573be403f301d65
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…