Trifluoroacetic acid → (S)-N-(4-(((4-fluorophenyl)(4-((S)-pyrrolidine-2-carboxamido)benzyl)amino)methyl)phenyl)-1-((R)-2-phenyl-2-(piperidin-1-yl)acetyl)pyrrolidine-2-carboxamide

HRID 923421Notes

Reaction equation

HRID 923421 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([NH:46][C:47]([C@@H:49]3[CH2:53][CH2:52][CH2:51][N:50]3C(OC(C)(C)C)=O)=[O:48])=[CH:42][CH:41]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([C@@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[C:24](=[O:38])[C@@H:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:18])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([C@@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[C:24](=[O:38])[C@@H:25]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)=[O:18])=[CH:12][CH:11]=2)[CH2:39][C:40]2[CH:45]=[CH:44][C:43]([NH:46][C:47]([C@@H:49]3[CH2:53][CH2:52][CH2:51][NH:50]3)=[O:48])=[CH:42][CH:41]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59540361(S)-tert-butyl 2-(4-(((4-fluorophenyl)(4-((S)-1-((R)-2-phenyl-2-(piperidin-1-yl)acetyl)pyrrolidine-2-carboxamido)benzyl)amino)methyl)phenylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 59540252(S)-N-(4-(((4-fluorophenyl)(4-((S)-pyrrolidine-2-carboxamido)benzyl)amino)methyl)phenyl)-1-((R)-2-phenyl-2-(piperidin-1-yl)acetyl)pyrrolidine-2-carboxamideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 114B (0.20 g, 0.24 mmol) was dissolved in dichloromethane (3 mL) and treated with trifluoroacetic acid (2 mL) at ambient temperature for 2 hours. The solution was concentrated, taken up in 25% isopropanol in chloroform, washed with sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated to give 0.16 g (91%) of the title compound.

Workup

  1. concentrationThe solution was concentrated
  2. washwashed with sodium bicarbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ad031361fc1547e6897e386698b0ccff
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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