Trifluoroacetic acid → HCID 10940042, compound
Reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([C@@H:16]([C:28](=[O:50])[N:29]([C@H:31]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:32]([N:34]1[CH2:38][CH2:37][CH2:36][C@H:35]1[CH2:39][N:40]([CH3:42])[CH3:41])=[O:33])[CH3:30])[CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)C)(C)(C)C>ClCCl>[CH2:43]([C@@H:31]([N:29]([CH3:30])[C:28](=[O:50])[C@H:16]([NH:14][CH3:13])[CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)[C:32]([N:34]1[CH2:38][CH2:37][CH2:36][C@H:35]1[CH2:39][N:40]([CH3:41])[CH3:42])=[O:33])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
At 0° C., trifluoroacetic acid (10 ml) was added to a solution of N-((1R)-1-{N-[(1R)-1-benzyl-2-((2S)-2-((dimethylamino)methyl)pyrrolidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamic acid tert-butyl ester.(1.37 g, 2.28 mmol) in dichloromethane (10 ml). The reaction mixture was stirred for 75 min at 0° C. The solvent was removed in vacuo. The residue was dissolved in dichloromethane (70 ml) and the solvent was removed in vacuo. The latter procedure was repeated two times. The crude product was purified by flash chromatography on silica (90 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 692 mg of (2R)-N-[(1R)-1-benzyl-2-((2S)-2-((dimethylamino)methyl)pyrrolidin-1-yl)-2-oxoethyl]-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide.
Workup
- customThe solvent was removed in vacuo
- dissolutionThe residue was dissolved in dichloromethane (70 ml)
- customthe solvent was removed in vacuo
- customThe crude product was purified by flash chromatography on silica (90 g)
Sources & evidence
- ORD record
- ord-58dd4346f4e541a29284a49cc7a615ec
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06919315B1
Reaction notes
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