2-Benzyloxy-6-(4-tert-butoxycarbonylaminobutoxy)-benzoic Acid Methyl Ester → 2-(4-Aminobutoxy)-6-benzyloxybenzoic Acid Methyl Ester

HRID 889276Notes

Reaction equation

HRID 889276 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15]C(OC(C)(C)C)=O)=[CH:8][CH:7]=[CH:6][C:5]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3](=[O:31])[C:4]1[C:5]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15]

Participants

3

Reactant 1

HCID 684315912-Benzyloxy-6-(4-tert-butoxycarbonylaminobutoxy)-benzoic Acid Methyl Ester

Product 1

HCID 684293722-(4-Aminobutoxy)-6-benzyloxybenzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 2-benzyloxy-6-(4-tert-butoxycarbonylamino-butoxy)-benzoic acid methyl ester (1.6 g, 3.7 mmol) in 30 mL of CH2Cl2/TFA (2:1) is stirred at RT for 20 min. The solvent is removed under reduced pressure and the residue is re-dissolved in CH2Cl2. The solution is washed with sat. NaHCO3, brine, and dried over sodium sulfate. The solvent is removed under reduced pressure to give the crude product as a colorless liquid. This is used directly in the next step.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue is re-dissolved in CH2Cl2
  3. washThe solution is washed with sat. NaHCO3, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-3f8d468cdf78461880226f4523f7d352
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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