Sodium Bicarbonate → HCID 69635154, compound

HRID 856252Notes

Reaction equation

HRID 856252 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][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:13][O:12]1.C(=O)([O-])O.[Na+]>C(O)C>[CH3:13][C@@:11]1([CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:20]2)[O:12][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 86604813HCID 86604813, compoundHCID 178526855HCID 178526855, compound

Product 1

HCID 69635154HCID 69635154, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (3.7 g, 25.1 mmol), ethyl (S)-1-(2-methyloxiran-2-ylmethyl)piperidine-4-carboxylate (4.8 g, 21.1 mmol) and sodium hydrogencarbonate (2.2 g, 25.1 mmol) in ethanol (25 ml) were stirred under reflux overnight. The reaction mixture was concentrated under reduced pressure. To the residue, water was added, and the solution was extracted with methylene chloride. The organic phase was washed with a saturated saline solution, dried over magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) and crystallized from diethyl ether to afford ethyl (S)-1-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperidine-4-carboxylate (1.4 g, yield 20%) as a white powder.

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue, water was added
  4. extractionthe solution was extracted with methylene chloride
  5. washThe organic phase was washed with a saturated saline solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe resulting filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1)
  10. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-3f6908de62794af2a4def2d1b97a0e97
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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