Sodium hydride → HCID 69481875, compound

HRID 856212Notes

Reaction equation

HRID 856212 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([O:14][CH2:15][C@@:16]([OH:28])([CH3:27])[CH2:17][N:18]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[N:20]=[C:19]1Cl)=[O:13])[CH2:7][CH2:6][CH2:5]2.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([O:14][CH2:15][C@:16]1([CH3:27])[O:28][C:19]3=[N:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][N:18]3[CH2:17]1)=[O:13])[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69481390HCID 69481390, compound

Product 1

HCID 69481875HCID 69481875, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 6-chloro-3,4-dihydro-2H-quinoline-1-carboxylate prepared in Example 116 (1.84 g, 4.29 mmol) in DMF (10 ml), sodium hydride (0.21 g, 5.15 mmol) was added followed by stirring for 1 hour with cooling on ice-bath. To the reaction mixture, ice-water was added, the solution was extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) and recrystallized from acetonitrile-isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 6-chloro-3,4-dihydro-2H-quinoline-1-carboxylate (0.68 g, yield 40%) as a white solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)
  7. customrecrystallized from acetonitrile-isopropanol

Sources & evidence

ORD record
ord-1c3f16ccdcc14adf92a632ea1d9e282b
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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