Sodium hydride → HCID 69481394, compound

HRID 856211Notes

Reaction equation

HRID 856211 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([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])[CH2:6][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)[CH2:8][N:7]([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])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69481269HCID 69481269, compound

Product 1

HCID 69481394HCID 69481394, compoundYield 50.1%

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-1H-isoquinoline-2-carboxylate prepared in Example 115 (0.26 g, 0.61 mmol) in DMF (2 ml), sodium hydride (30 mg, 0.73 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, concentrated under reduced pressure and recrystallized from isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 6-chloro-3,4-dihydro-1H-isoquinoline-2-carboxylate (0.12 g, 49%) 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. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-b113865ab15a4d1f972dbfca375550d4
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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