Benzyl Bromide → HCID 69799007, compound

HRID 353269Notes

Reaction equation

HRID 353269 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C:12]([N:14]([CH3:28])[C@@H:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CC(C)=O>[CH2:35]([O:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C:12]([N:14]([CH3:28])[C@@H:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:13])=[CH:4][CH:3]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 69797659HCID 69797659, compound

Product 1

HCID 69799007HCID 69799007, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of compound (vi) (3.2 g, 7.62 mmol) in anhydrous acetone (50 mL) was added anhydrous potassium carbonate (4.22 g, 30.5 mmol). The mixture was stirred at room temperature for 30 mins then added dropwise benzyl bromide (1.30 g, 7.62 mmol). The stirring was continued for an additional 48 h and the reaction mixture was filtered off. The cake was washed thoroughly with acetone and the combined-filtrate was evaporated to dryness. The residue was redissolved in CH2Cl2 and the organic layer was washed with water, saturated salt solution and dried over anhydrous sodium sulfate. The removal of the solvent resulted in a yellow foam, and the product was purified on a silica gel column to give (vii) as a solid, 2.5 g (69%); MS 474 (M+H)+.

Workup

  1. waitThe stirring was continued for an additional 48 h
  2. filtrationthe reaction mixture was filtered off
  3. washThe cake was washed thoroughly with acetone
  4. customthe combined-filtrate was evaporated to dryness
  5. dissolutionThe residue was redissolved in CH2Cl2
  6. washthe organic layer was washed with water, saturated salt solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe removal of the solvent
  9. customresulted in a yellow foam
  10. customthe product was purified on a silica gel column

Sources & evidence

ORD record
ord-ef2c7819ff1240a485a5270efdaeb7de
Source dataset
uspto-grants-2004_06
Patent number
US06750216B2

Reaction notes

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