Trifluoroacetic acid → HCID 67497288, compound

HRID 1628293Notes

Reaction equation

HRID 1628293 reaction equation
[O:1]=[C:2]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH:26]=2)[CH2:21][CH2:20]1)[C@@H:3]([NH:11]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:11][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:2]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH:26]=2)[CH2:21][CH2:20]1)=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69620884HCID 69620884, compound

Product 1

HCID 67497288HCID 67497288, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 ml flask was added (S)-tert-butyl 1-oxo-3-phenyl-1-(6-(pyridin-4-yl)indolin-1-yl)propan-2-ylcarbamate 50.D (300 mg, 0.68 mmole) 10 ml of CH2Cl2, and 5 ml of TFA. The reaction was stirred at room temperature for 3 hour at which time the solvent was removed with a stream of nitrogen. The crude was resuspended and the solvent was removed as before. This procedure was repeated one more time to give (S)-2-amino-3-phenyl-1-(6-(pyridin-4-yl)indolin-1-yl)propan-1-one 50.E of as a light yellow oil (300 mg, 21% yield).

Workup

  1. customwas removed with a stream of nitrogen
  2. customthe solvent was removed as before

Sources & evidence

ORD record
ord-7fb468ec869844619e55653acb2b3741
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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