Water → HCID 69480010, compound

HRID 856271Notes

Reaction equation

HRID 856271 reaction equation
Cl[C:2]1[N:3]([CH2:10][C@@:11]([CH3:26])([OH:25])[CH2:12][N:13]2[CH2:18][CH:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+].O>CN(C=O)C>[CH3:26][C@@:11]1([CH2:12][N:13]2[CH2:18][CH:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[O:25][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 962WaterHCID 24758Sodium hydrideHCID 69479031HCID 69479031, compound

Product 1

HCID 69480010HCID 69480010, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-1-(2-Chloro-4-nitro-imidazol-1-yl)-2-methyl-3-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)propan-2-ol prepared in Example 275 (0.492 g, 1.31 mmol) was dissolved in DMF (8 ml). To the solution, sodium hydride (63 mg, 1.57 mmol) was added with cooling on ice-bath followed by stirring at room temperature for 3 hours. To the reaction mixture, water was added. After extraction with ethyl acetate, the organic phase was washed with water and a saturated saline solution, dried over sodium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/acetone=4/1) and recrystallized from methylene chloride-ethyl acetate to afford (S)-2-methyl-6-nitro-2-(4-phenyl-1,2,3,6-tetrahydropyridin-1-ylmethyl)-2,3-dihydroimidazo[2,1-b]oxazole (0.059 g, yield 13%) as a light yellow solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. extractionAfter extraction with ethyl acetate
  3. washthe organic phase was washed with water
  4. dry with materiala saturated saline solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe resulting filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane/acetone=4/1)
  8. customrecrystallized from methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-12a9f99dd71046248d725a017f489602
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…