Benzyl Bromide → HCID 58975532, compound

HRID 1643872Notes

Reaction equation

HRID 1643872 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H: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][C@H: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 58975517HCID 58975517, compound

Product 1

HCID 58975532HCID 58975532, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirring mixture of 87E (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-50a7218bcc49413796439760dbf21208
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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