Trifluoroacetic acid → HCID 9830936, compound

HRID 896929Notes

Reaction equation

HRID 896929 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=[O:61])[N:24]([C@@H:26]([C:38](=[O:60])[N:39]([C@H:41]([CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:42]([N:44]2[CH2:48][CH2:47][CH2:46][C@H:45]2[CH2:49][N:50]([CH3:52])[CH3:51])=[O:43])[CH3:40])[CH2:27][C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)[CH3:25])[CH:18]=1)C)(C)(C)C>ClCCl>[CH2:53]([C@@H:41]([N:39]([CH3:40])[C:38]([C@H:26]([N:24]([CH3:25])[C:23](=[O:61])[C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH2:16][NH:14][CH3:13])[CH:18]=1)[CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=1)=[O:60])[C:42]([N:44]1[CH2:48][CH2:47][CH2:46][C@H:45]1[CH2:49][N:50]([CH3:51])[CH3:52])=[O:43])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11007145HCID 11007145, compound

Product 1

HCID 9830936HCID 9830936, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., trifluoroacetic acid (7 ml) was added to a solution of N-(3-[N-((1R)-1-{N-[(1R)-1-benzyl-2-((2S)-2-((dimethylamino)methyl)pyrrolidin-1-yl)-2-oxoethyl]-N-methylcarbamoyl}-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]benzyl}-N-methylcarbamic acid tert-butyl ester (523 mg, 0.70 mmol) in dichloromethane (7 ml). The reaction mixture was stirred for 25 min at 0° C. The solvent was removed in vacuo. The residue was dissolved in dichloromethane (90 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 (40 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 436 mg of the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (90 ml)
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by flash chromatography on silica (40 g)

Sources & evidence

ORD record
ord-76796658bcf44d83a444974e538dcfcb
Source dataset
uspto-grants-2005_07
Patent number
US06919315B1

Reaction notes

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