Sodium hydride → HCID 69481241, compound

HRID 856209Notes

Reaction equation

HRID 856209 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([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])[CH2:6][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)[N:7]([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])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69481004HCID 69481004, compound

Product 1

HCID 69481241HCID 69481241, compoundYield 55%

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-2,3-dihydroindole-1-carboxylate prepared in Example 113 (0.60 g, 1.44 mmol) in DMF (6 ml), sodium hydride (70 mg, 1.73 mmol) was added followed by stirring 1 hour with cooling on ice-bath. To the reaction mixture, ice-water was added, and the precipitates were filtered off, washed with water and recrystallized from acetonitrile-isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 5-chloro-2,3-dihydroindole-1-carboxylate (0.30 g, yield 55%) as a white solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. filtrationthe precipitates were filtered off
  3. washwashed with water
  4. customrecrystallized from acetonitrile-isopropanol

Sources & evidence

ORD record
ord-f92c072042af4d189ea354cad0f144ba
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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