Sodium Acetate → 2-(4-Tert-butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

HRID 856278Notes

Reaction equation

HRID 856278 reaction equation
Cl[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)C.[Na+]>C(O)CC.C(Cl)Cl>[C:24]([O:23][C:21]([N:18]1[CH2:17][CH2:16][N:15]([CH2:14][C:11]2([CH3:13])[O:12][C:2]3=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]3[CH2:10]2)[CH2:20][CH2:19]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 23081489Tert-butyl 4-(2-methyloxiran-2-ylmethyl)-piperazine-1-carboxylateHCID 178526855HCID 178526855, compound

Product 1

HCID 230810802-(4-Tert-butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazoleYield 23.3%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (3.19 g, 21.6 mmol) and tert-butyl 4-(2-methyloxiran-2-ylmethyl)-piperazine-1-carboxylate (5.53 g, 21.6 mmol) and sodium acetate (1.95 g, 23.8 mmol) were dissolved in 1-propanol (50 ml) followed by stirring under reflux for 48 hours. The reaction mixture was diluted with methylene chloride. The solution was washed with water and a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) and treated with methylene chloride-diisopropyl ether to afford 2-(4-tert-butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (1.85 g, yield 23%) as a white powder.

Workup

  1. temperatureunder reflux for 48 hours
  2. washThe solution was washed with water
  3. dry with materiala saturated saline solution, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)
  7. additiontreated with methylene chloride-diisopropyl ether

Sources & evidence

ORD record
ord-eca063392a804a40b293e7142b2b0389
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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