Water → tert-Butyl 4-[N-(5-bromo-2-benzyloxybenzyl)-N-(4-methoxycarbonylbenzyl)amino]benzoate

HRID 1106817Notes

Reaction equation

HRID 1106817 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:6]([CH:22]=1)[CH2:7][NH:8][C:9]1[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][CH:10]=1.[CH3:31][O:32][C:33](=[O:42])[C:34]1[CH:39]=[CH:38][C:37]([CH2:40]Br)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[C:6]([CH:22]=1)[CH2:7][N:8]([C:9]1[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][CH:10]=1)[CH2:40][C:37]1[CH:36]=[CH:35][C:34]([C:33]([O:32][CH3:31])=[O:42])=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 22675479tert-Butyl 4-[5-bromo-2-benzyloxybenzylamino]benzoate

Product 1

HCID 22675539tert-Butyl 4-[N-(5-bromo-2-benzyloxybenzyl)-N-(4-methoxycarbonylbenzyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 4-[5-bromo-2-benzyloxybenzylamino]benzoate (16.9 g) and methyl-4-bromomethylbenzoate were dissolved in dimethylformamide (30 ml) and potassium carbonate (18 g) added. The mixture was stirred at ambient temperature for 24 hours and then poured into water (300 ml). The reaction mixture was extracted with ether (4×100 ml). The combined ether extracts were washed with water (3×100 ml) and brine (1×100 ml), dried over magnesium sulphate and evaporated. The residue was purified by MPLC eluting with 1:1 dichloromethane/hexane to give tert-butyl 4-[N-(5-bromo-2-benzyloxybenzyl)-N-(4-methoxycarbonylbenzyl)amino]benzoate (3.6 g) m.p. 154-155° C.

Workup

  1. extractionThe reaction mixture was extracted with ether (4×100 ml)
  2. washThe combined ether extracts were washed with water (3×100 ml) and brine (1×100 ml)
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by MPLC
  6. washeluting with 1:1 dichloromethane/hexane

Sources & evidence

ORD record
ord-7e9bf63f9b734000998c1f65b8650ce5
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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