Trifluoroacetic acid → HCID 10940042, compound

HRID 2104335Notes

Reaction equation

HRID 2104335 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]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11061050HCID 11061050, compound

Product 1

HCID 10940042HCID 10940042, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (70 ml)
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by flash chromatography on silica (90 g)

Sources & evidence

ORD record
ord-cec220f22e60481ea27dec3bcfa32652
Source dataset
uspto-grants-2009_08
Patent number
US07576062B2

Reaction notes

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