Trifluoroacetic acid → HCID 131726574, compound

HRID 856336Notes

Reaction equation

HRID 856336 reaction equation
C([O:5][C:6](=[O:27])[NH:7][N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2([CH3:26])[O:19][C:18]3=[N:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][N:17]3[CH2:16]2)[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.C(N(CC)CC)C.ClC(O[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=O.C(=O)([O-])O.[Na+]>>[CH2:46]([O:5][C:6](=[O:27])[NH:7][N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2([CH3:26])[O:19][C:18]3=[N:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][N:17]3[CH2:16]2)[CH2:12][CH2:13]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 91438393HCID 91438393, compound

Product 1

HCID 131726574HCID 131726574, compoundYield 4%

Procedure

A mixture of tert-butyl[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]carbamate prepared in Example 493-(150 mg, 0.39 mmol) and trifluoroacetic acid (4 ml) was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methylene chloride (4 ml) and neutralized with triethylamine (4 ml, 28.7 mmol). Subsequently, to the solution, benzyl chloroformate (100 mg, 0.59 mmol) was added with cooling on ice-bath followed by stirring at room temperature for 2 hours. To the reaction mixture, a saturated sodium hydrogencarbonate solution was added. The mixture was extracted with methylene chloride. The extract was washed with water and a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/acetone=1/1) to afford benzyl[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]carbamate (6.5 mg, yield 4%) as a light yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride (4 ml)
  3. temperaturewith cooling on ice-bath
  4. stirringby stirring at room temperature for 2 hours
  5. extractionThe mixture was extracted with methylene chloride
  6. washThe extract was washed with water
  7. dry with materiala saturated saline solution, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (n-hexane/acetone=1/1)

Sources & evidence

ORD record
ord-a4ed0c4d0f1549afbdee4706e90ec1a9
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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