Benzyl Bromide → HCID 58975524, compound

HRID 1178780Notes

Reaction equation

HRID 1178780 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:18])[CH:15]=2)[NH:10][C:9]1=[O:19])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC(C)=O>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:18])[CH:15]=2)[N:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]1=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58975528HCID 58975528, compound

Product 1

HCID 58975524HCID 58975524, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirring mixture of 3B (0.60 g, 1.76 mmol), K2CO3 (0.49 g, 3.52 mmol), and benzyl bromide (0.36 g, 2.11 mmol) in acetone (15 mL) was heated to reflux under argon for 16 h. The mixture was then cooled to RT and the solvent was evaporated under vacuum. The resulting residue was partitioned between water and EtOAc. The EtOAc layer was washed with brine, dried (Na2SO4), and evaporated. The resulting crude product was chromatographed on silica gel eluted with 10-20% EtOAc in hexane (step-wise gradient) to obtain the title compound (0.72 g) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 16 h
  3. customthe solvent was evaporated under vacuum
  4. customThe resulting residue was partitioned between water and EtOAc
  5. washThe EtOAc layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe resulting crude product was chromatographed on silica gel
  9. washeluted with 10-20% EtOAc in hexane (step-wise gradient)

Sources & evidence

ORD record
ord-bde252f71cef479aa97c7e3b24341e60
Source dataset
uspto-grants-2007_10
Patent number
US07276608B2

Reaction notes

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