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

HRID 1866509Notes

Reaction equation

HRID 1866509 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 33) (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-801fac61f31f44e5aad08babb3436a8b
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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