Benzyl Bromide → HCID 23378122, compound

HRID 1007687Notes

Reaction equation

HRID 1007687 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1CCN2C(=NCCC2)CC1.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(#N)C>[CH2:32]([O:19][C:18](=[O:20])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([I:17])=[CH:15][CH:16]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2755956(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid

Product 1

HCID 23378122HCID 23378122, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Boc-4-iodophenylalanine was dissolved in acetonitrile and DBU (1 equivalent) was added followed by benzyl bromide (1 equivalent). The mixture was stirred for 2 h at room temperature. After removal of the solvent under reduced pressure, the residue was dissolved in EtOAc and the solution washed with 10% aqueous HCl and water. Drying (MgSO4) and concentration under reduced pressure gave a crude product that was purified by crystallization from hexane.

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washthe solution washed with 10% aqueous HCl and water
  4. customDrying
  5. concentration(MgSO4) and concentration under reduced pressure

Sources & evidence

ORD record
ord-a2b19327e8b142bebae1fa1df6707860
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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