Trifluoroacetic acid → 4-(1-Phenylcyclohexyl)phenyl 2-amino-3-methylbutanoate

HRID 70730Notes

Reaction equation

HRID 70730 reaction equation
[C:1]1([C:7]2([C:13]3[CH:33]=[CH:32][C:16]([O:17][C:18]([CH:20]([NH:24]C(=O)OC(C)(C)C)[CH:21]([CH3:23])[CH3:22])=[O:19])=[CH:15][CH:14]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][CH:20]([CH:21]([CH3:23])[CH3:22])[C:18]([O:17][C:16]1[CH:32]=[CH:33][C:13]([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:14][CH:15]=1)=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66967822Tert-butyl 1-((4-(1-phenylcyclohexyl)phenoxy)carbonyl)-2-methylpropylcarbamate

Product 1

HCID 669681234-(1-Phenylcyclohexyl)phenyl 2-amino-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution at room temperature of tert-butyl 1-((4-(1-phenylcyclohexyl)phenoxy)carbonyl)-2-methylpropylcarbamate (142 mg, 0.31 mmol) in dry DCM (3 mL) was added TFA (300 μL), which caused gas evolution. Stirring was continued. After 1 h the reaction mixture was concentrated in vacuo to afford 96 mg (0.21 mmol; 67%) of colourless oil. LC-MS purity (UV/MS): 92/97%, Rt 5.45 min, M+1: 352.49. 1H NMR (400 MHz, CDCl3): 11.12 (br s), 7.76 (br s), 7.29 (d, 2H, J=8.8 Hz), 7.27 (d, 4H, J=4.8 Hz), 7.13-7.16 (m, 1H), 6.95 (d, 2H, J=8.8 Hz), 6.16 (d, 1H, J=4.0 Hz), 2.40-2.48 (m, 1H), 2.18-2.33 (m, 4H), 1.50-1.58 (m, 6H), 1.05-1.08 (m, 6H).

Workup

  1. concentrationAfter 1 h the reaction mixture was concentrated in vacuo
  2. customto afford 96 mg (0.21 mmol; 67%) of colourless oil

Sources & evidence

ORD record
ord-96140d3812354d92b5f4a0423c6d7a2e
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Reaction notes

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