Trifluoroacetic acid → Methyl 4-({2-[2-(4-bromobenzyloxy)phenyl]ethylamino}methyl)benzoate

HRID 1672611Notes

Reaction equation

HRID 1672611 reaction equation
[Br:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][CH2:15][N:16]([CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=2)C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][CH2:15][NH:16][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=2)=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57864402Methyl 4-[({2-[2-(4-bromobenzyloxy)phenyl]ethyl}-tert-butoxycarbonylamino)methyl]benzoate

Product 1

HCID 22014995Methyl 4-({2-[2-(4-bromobenzyloxy)phenyl]ethylamino}methyl)benzoateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.2 g (7.57 mmol) of methyl 4-[({2-[2-(4-bromobenzyloxy)phenyl]ethyl}-tert-butoxycarbonylamino)methyl]benzoate from Example 4A in 15 ml of dichloromethane is stirred with 15 ml of trifluoroacetic acid at room temperature for 4 hours. The reaction solution is then neutralized with aqueous sodium bicarbonate solution, and the organic phase is separated off and dried over sodium sulfate. Filtration is followed by removal of the solvent in vacuo. 3.2 g (7.04 mmol, 92% yield) of a colorless oil are obtained which are employed in the next stage without further purification.

Workup

  1. customthe organic phase is separated off
  2. dry with materialdried over sodium sulfate
  3. filtrationFiltration
  4. customis followed by removal of the solvent in vacuo

Sources & evidence

ORD record
ord-ce317b1ed501428c99a18934d614935e
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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