Trifluoroacetic acid → (S)-2-Amino-1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-one

HRID 2299892Notes

Reaction equation

HRID 2299892 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:13]([N:15]1[CH2:20][CH2:19][CH:18]([N:21]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:29][CH:28]=2)[CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH2:17][CH2:16]1)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@@H:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:13]([N:15]1[CH2:20][CH2:19][CH:18]([N:21]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:31][CH:32]=2)[CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH2:17][CH2:16]1)=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10840671(S)-(1-{4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidine-1-carbonyl}-3-methyl-butyl)-carbamic acid tert-butyl ester

Product 1

HCID 10004622(S)-2-Amino-1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-(1-{4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidine-1-carbonyl}-3-methyl-butyl)-carbamic acid tert-butyl ester (1.07 g, 1.90 mmol) was dissolved in CH2Cl2 (4.5 mL) and treated with TFA (4.5 mL). The reaction was stirred for 25 minutes, then concentrated in vacuo. The residue was dissolved in EtOAc (175 mL) and solution was washed twice with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated in vacuo to give 0.87 g (99%) of the desired product as a pale oil.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (175 mL)
  3. washsolution was washed twice with saturated bicarbonate solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8ccfc9d2c5a42b89598cfadeb3582c4
Source dataset
uspto-grants-2002_12
Patent number
US06495715B2

Reaction notes

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