Sodium hydride → HCID 69479050, compound

HRID 856210Notes

Reaction equation

HRID 856210 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([O:13][CH2:14][C@@:15]([OH:27])([CH3:26])[CH2:16][N:17]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[N:19]=[C:18]1Cl)=[O:12])[CH2:5]2.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([O:13][CH2:14][C@:15]1([CH3:26])[O:27][C:18]3=[N:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][N:17]3[CH2:16]1)=[O:12])[CH2:5]2

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69481382HCID 69481382, compound

Product 1

HCID 69479050HCID 69479050, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 5-chloro-1,3-dihydro-isoindol-2-carboxylate prepared in Example 114 (0.13 g, 0.31 mmol) in DMF (2 ml), sodium hydride (15 mg, 0.37 mmol) was added followed by stirring for 1 hour with cooling on ice-bath. To the reaction mixture, ice-water was added, and 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 (ethyl acetate) to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 5-chloro-1,3-dihydroisoindole 2-carboxylate (7 mg, yield 6%) as a light yellow 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 (ethyl acetate)

Sources & evidence

ORD record
ord-a1fe6e74065c4cf68aa63180ae96096b
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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