Trifluoroacetic acid → (S)-N-(4-((phenyl(4-((E)-2-((S)-pyrrolidin-2-yl)vinyl)benzyl)amino)methyl)phenyl)pyrrolidine-2-carboxamide

HRID 923450Notes

Reaction equation

HRID 923450 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1/[CH:13]=[CH:14]/[C:15]1[CH:50]=[CH:49][C:18]([CH2:19][N:20]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35]([C@@H:37]3[CH2:41][CH2:40][CH2:39][N:38]3C(OC(C)(C)C)=O)=[O:36])=[CH:30][CH:29]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:21]1([N:20]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([NH:34][C:35]([C@@H:37]3[CH2:41][CH2:40][CH2:39][NH:38]3)=[O:36])=[CH:32][CH:33]=2)[CH2:19][C:18]2[CH:17]=[CH:16][C:15](/[CH:14]=[CH:13]/[C@@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[CH:50][CH:49]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59540362(S)-tert-butyl 2-(4-(((4-((E)-2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)vinyl)benzyl)(phenyl)amino)methyl)phenylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 66749838(S)-N-(4-((phenyl(4-((E)-2-((S)-pyrrolidin-2-yl)vinyl)benzyl)amino)methyl)phenyl)pyrrolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 149G (50 mg, 0.073 mmol) dissolved in dichloromethane (0.3 mL) was added trifluoroacetic acid (2.7 mL) and the resultant solution stirred at room temperature for 20 minutes. The solution was then concentrated under vacuum, the residue dissolved in a chloroform/isopropanol mixture and extracted with aqueous sodium bicarbonate, the organic solution was then dried, filtered, and concentrated to afford the title compound. m/z 481 (M+H)+.

Workup

  1. concentrationThe solution was then concentrated under vacuum
  2. dissolutionthe residue dissolved in a chloroform/isopropanol mixture
  3. extractionextracted with aqueous sodium bicarbonate
  4. customthe organic solution was then dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9d03c6252f374ad6bc466bc06985a63f
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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