Sodium hydride → (R)-2-methoxymethoxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

HRID 856164Notes

Reaction equation

HRID 856164 reaction equation
[H-].[Na+].Cl[C:4]1[N:5]([CH2:12][C@:13]([OH:20])([CH3:19])[CH2:14][O:15][CH2:16][O:17][CH3:18])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[N:8]=1>CN(C=O)C>[CH3:18][O:17][CH2:16][O:15][CH2:14][C@:13]1([CH3:19])[O:20][C:4]2=[N:8][C:7]([N+:9]([O-:11])=[O:10])=[CH:6][N:5]2[CH2:12]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69481666(R)-2-chloro-1-(2-hydroxy-3-methoxymethoxy-2-methylpropyl)-4-nitroimidazole

Product 1

HCID 69480830(R)-2-methoxymethoxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazoleYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.0 g, 25 mmol) was added to a solution of (R)-2-chloro-1-(2-hydroxy-3-methoxymethoxy-2-methylpropyl)-4-nitroimidazole prepared in Example 27 (6.0 g, 21 mmol) in DMF (30 ml) with cooling on ice-bath followed by stirring at room temperature for 1.5 hours. Ice-water was added to the reaction mixture, and the precipitates were filtered off and washed with water to afford (R)-2-methoxymethoxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (3.1 g, yield 59%) as a yellow solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. filtrationthe precipitates were filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-7b735d9ee92d48cb8de59087843de939
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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