Trifluoroacetic acid → 3-[Benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-propionic acid

HRID 491909Notes

Reaction equation

HRID 491909 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][CH:8]([N:15]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:24]([N:15]([CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[CH:8]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[CH2:7][C:6]([OH:31])=[O:5])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670236593-[Benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-propionic acid tert-butyl ester

Product 1

HCID 670236463-[Benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-propionic acid tert-butyl ester (13.7 g, 32.5 mmol) in dichloromethane (65 mL) at 0° C., trifluoroacetic acid (65 mL) was slowly added (over 30 min). The reaction mixture was then stirred for 2 hours at room temperature. The solvent was evaporated and the residue azeotroped (3×50 ml, toluene) to yield a residue.

Workup

  1. customThe solvent was evaporated
  2. customthe residue azeotroped (3×50 ml, toluene)
  3. customto yield a residue

Sources & evidence

ORD record
ord-16e593adfbbe464db46e2b772e9fd75c
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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