Isopropyl iodide → HCID 67103841, compound

HRID 2080825Notes

Reaction equation

HRID 2080825 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:23])[NH:13][C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=1[NH2:22])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH:28]([CH3:30])[CH3:29]>CN(C=O)C>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:23])[N:13]([C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=1[NH2:22])[CH:28]([CH3:30])[CH3:29])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 67103843HCID 67103843, compound

Product 1

HCID 67103841HCID 67103841, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (242 mg) obtained in Example 45-3 was dissolved in DMF (5.0 ml). The solution was added with 60% sodium hydride (29.1 mg) and then 2-iodopropane (79.6 μl) in an ice bath. The whole was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off. The resultant was dissolved in chloroform and added with distilled water and the whole was stirred for a while. The solution was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (44.1 mg) as a pale-yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe resultant was dissolved in chloroform
  4. additionadded with distilled water
  5. stirringthe whole was stirred for a while
  6. extractionThe solution was subjected to extraction with chloroform
  7. washwashed with a saturated saline solution
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e3d573c2b958463bb808084fc31a278b
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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