Trifluoroacetic acid → (2S)-2-Amino-6-(4-oxo-4-phenylbutyrylamino)hexanoic acid amide

HRID 2112418Notes

Reaction equation

HRID 2112418 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C@H:15]([C:33](=[O:35])[NH2:34])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:32])[CH2:22][CH2:23][C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(C)(C)C>ClCCl>[NH2:14][C@@H:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:32])[CH2:22][CH2:23][C:24](=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:33]([NH2:34])=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57642044[(1S)-1-carbamoyl-5-(4-oxo-4-phenylbutyrylamino)pentyl]carbamic acid tert-butyl ester

Product 1

HCID 11220467(2S)-2-Amino-6-(4-oxo-4-phenylbutyrylamino)hexanoic acid amideYield 21.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (25 ml) was added to a solution of [(1S)-1-carbamoyl-5-(4-oxo-4-phenylbutyrylamino)pentyl]carbamic acid tert-butyl ester (0.56 g, 1.38 mmol) in dichloromethane (25 ml). The reaction mixture was stirred for 1 h at room temperature. The solvent was removed. The crude product was purified by HPLC on a RP-18 column, using a gradient of 20-45% acetonitrile in water, containing 0.1% of trifluoracetic acid as buffer to give 92 mg of the title compound with a purity of approx. 85%, which was used for the further experiments.

Workup

  1. customThe solvent was removed
  2. customThe crude product was purified by HPLC on a RP-18 column
  3. additioncontaining 0.1% of trifluoracetic acid as buffer

Sources & evidence

ORD record
ord-3807b82f94674c1ab2e075cc5cdf486d
Source dataset
uspto-grants-2009_04
Patent number
US07524813B2

Reaction notes

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