Benzyl Bromide → HCID 23378122, compound

HRID 1280071Notes

Reaction equation

HRID 1280071 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].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH2:21]([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:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 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 DUB (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. additionDUB (1 equivalent) was added
  2. customAfter removal of the solvent under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAc
  4. washthe solution washed with 10% aqueous HCl and water
  5. customDrying
  6. concentration(MgSO4) and concentration under reduced pressure

Sources & evidence

ORD record
ord-3c139ecfcadf49529fd368c4ea98e0aa
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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