Trifluoroacetic acid → HCID 22879058, compound

HRID 2293452Notes

Reaction equation

HRID 2293452 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:43])[C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH2:18][C@@H:19]([NH:24][C:25](=[O:42])[C@@H:26]([NH:34]C(OC(C)(C)C)=O)[CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:43])[C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH2:18][C@@H:19]([NH:24][C:25](=[O:42])[C@@H:26]([NH2:34])[CH2:27][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22879057HCID 22879057, compound

Product 1

HCID 22879058HCID 22879058, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[2-(S)-[[2-(S)-[[(1,1-dimethylethoxy)-carbonyl]amino]-1-oxo-3-cyclohexylpropyl]amino]-4-methylpentyl]-L-proline 4-phenylbutylamide (62.8 mg, 104 mmol) in dichloromethane (5 mL) was treated with trifluoroacetic acid (3.0 mL). After TLC indicated the reaction was complete, the mixture was concentrated to a residue, taken up in fresh dichloromethane (10 mL) and washed with satd. aq. NaHCO3 and dried (MgSO4). The solution was concentrated to an oil and chromatographed with acidic silica to provide 48.8 mg of the the title compound. The 1H NMR and Mass spectrum analysis of this compound was consistent with the structure.

Workup

  1. concentrationthe mixture was concentrated to a residue
  2. washwashed with satd
  3. dry with materialaq. NaHCO3 and dried (MgSO4)
  4. concentrationThe solution was concentrated to an oil
  5. customchromatographed with acidic silica

Sources & evidence

ORD record
ord-b4ddbe2542ce4ce9907078ac7f54bb3b
Source dataset
uspto-grants-1997_11
Patent number
US05686469

Reaction notes

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