Trifluoroacetic acid → Methyl 3-(2-amino-2-methylpropyl)benzoate

HRID 494422Notes

Reaction equation

HRID 494422 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([NH:14]C(OC(C)(C)C)=O)([CH3:13])[CH3:12])[CH:5]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([NH2:14])([CH3:12])[CH3:13])[CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597135613-(2-tert-Butoxycarbonylamino-2-methylpropyl)benzoic acid methyl ester

Product 1

HCID 57516949Methyl 3-(2-amino-2-methylpropyl)benzoateYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-tert-butoxycarbonylamino-2-methylpropyl)benzoic acid methyl ester (Preparation 20) (1.6 g, 5.2 mmol) in dichloromethane (160 mL) at 0° C. was treated with trifluoroacetic acid (13.6 mL) and left to warm to room temperature over 2 hours. The solvent was removed in vacuo and the product purified by cation exchange chromatography (methanol followed by 2M ammonia in methanol) to yield the title compound as an amber oil (1.06 g).

Workup

  1. waitleft
  2. customThe solvent was removed in vacuo
  3. customthe product purified by cation exchange chromatography (methanol followed by 2M ammonia in methanol)

Sources & evidence

ORD record
ord-ed8c687b7deb400d9be455c7c47a6594
Source dataset
uspto-grants-2009_05
Patent number
US07538141B2

Reaction notes

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