Benzyl Bromide → 3-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-bromo-benzoic acid benzyl ester

HRID 554583Notes

Reaction equation

HRID 554583 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[Br:24])[C:18]([OH:20])=[O:19])[CH2:12][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CC#N>[CH2:31]([O:19][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][C:23]([Br:24])=[C:15]([CH2:14][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12][CH3:13])[CH:16]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 574198643-[(Benzyloxycarbonyl-ethyl-amino)-methyl]-4-bromo-benzoic acid

Product 1

HCID 585652093-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-bromo-benzoic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-bromo-benzoic acid (8.9 g, 22.6 mmol) in MeCN (400 mL) was added cesium carbonate (18.4 g, 56.5 mmol), followed by benzyl bromide (2.95 mL, 24.9 mmol), and the reaction was stirred at room temperature overnight. The mixture was filtered and extracted with EtOAc and washed with H2O. The organic layer was dried and concentrated, and the residue was purified by silica gel chromatography (0-25% EtOAc in hexanes) to give 3-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-bromo-benzoic acid benzyl ester.

Workup

  1. filtrationThe mixture was filtered
  2. extractionextracted with EtOAc
  3. washwashed with H2O
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography (0-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ab7a9e55c85b48be8ba170a94e92b110
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

Loading…