Ethanol → tert-Butyl 4-[5-bromo-2-benzyloxybenzylamino]benzoate

HRID 1106816Notes

Reaction equation

HRID 1106816 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7](O)=O.[C:19]([O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)([CH3:22])([CH3:21])[CH3:20].C(O)C.[BH4-].[Na+]>O.O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[CH2:7][NH:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]([O:23][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:32])=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 24613572-(Benzyloxy)-5-bromobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 22675479tert-Butyl 4-[5-bromo-2-benzyloxybenzylamino]benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-2-benzyloxybenzoic acid [International patent application, publication no, WO 96/03380] and tert-butyl-4-aminobenzoate were heated on a steam bath for 2 hours. Ethanol (50 ml) and tetrahydrofuran (50 ml) were added to the hot reaction mixture. The solution was allowed to cool and sodium borohydride (1.4 g) was added. The reaction mixture was then stirred at ambient temperature for 3 hours, poured into water (200 ml) and extracted with dichloromethane (4×100 ml). The combined extracts were dried over magnesium sulphate to give tert-butyl 4-[5-bromo-2-benzyloxybenzylamino]benzoate which was used without further purification (18 g).

Workup

  1. temperatureto cool
  2. extractionextracted with dichloromethane (4×100 ml)
  3. dry with materialThe combined extracts were dried over magnesium sulphate

Sources & evidence

ORD record
ord-6f7be7f2db46459aaf1cf73aa521f900
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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