Benzyl Bromide → HCID 68746130, compound

HRID 333324Notes

Reaction equation

HRID 333324 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:28]1[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][CH:29]=1>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([O:12][CH2:34][C:31]2[CH:32]=[CH:33][CH:28]=[CH:29][CH:30]=2)=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 448910052-[(4-Bromophenyl)methyl]-3-[(tert-butoxycarbonyl)amino]propanoic acid

Product 1

HCID 68746130HCID 68746130, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of 3-(4-bromo-phenyl)-2-(tert-butoxycarbonylamino-methyl)-propionic acid (496 mg, 1.385 mmol), K2CO3 (383 mg, 2.77 mmol) and BnBr (0.493 ml, 4.15 mmol) in DMF (3 ml) was allowed to stir under nitrogen for 60 hours. The reaction mixture was cooled, and brine was added. The product was extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 50:50) and then purified by RP-HPLC (XBridge Prep Phenyl OBD, H2O (0.1% NH4OH)/CH3CN) to give benzyl 2-(4-bromobenzyl)-3-(tert-butoxycarbonylamino)propanoate (44 mg); Retention time=1.67 minutes (condition B); MS (ES+)=348.0 (m-Boc+2).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe product was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 50:50)
  8. custompurified by RP-HPLC (XBridge Prep Phenyl OBD, H2O (0.1% NH4OH)/CH3CN)

Sources & evidence

ORD record
ord-961a8c8010f9448a8efc1f7f2f70ed13
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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