Trifluoroacetic acid → HCID 67496285, compound

HRID 1628311Notes

Reaction equation

HRID 1628311 reaction equation
[C:1]([C:4]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][N:8]2[C:19](=[O:36])[C@@H:20]([NH:28]C(=O)OC(C)(C)C)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:28][C@@H:20]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:19]([N:8]1[C:9]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:12]=[C:4]([C:1]([NH2:2])=[O:3])[C:5]=2[CH2:6][CH2:7]1)=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69620934HCID 69620934, compound

Product 1

HCID 67496285HCID 67496285, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 ml vial was added crude (S)-tert-butyl 1-(4-carbamoyl-6-(pyridin-4-yl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate 60.B (75 mg, 0.1 mmole), 20 ml of DCM and 10 ml of TFA. The reaction was stirred at room temperature for 12 hours at which time the crude was partitioned between 600 ml DCM and 100 ml saturated sodium carbonate. The organic layer was extracted once more with 100 ml of water, the organic layer dried with sodium sulfate and the solvent removed to give (S)-1-(2-amino-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxamide 60.0 as an off white solid. (49 mg, 82% yield).

Workup

  1. customwas partitioned between 600 ml DCM and 100 ml saturated sodium carbonate
  2. extractionThe organic layer was extracted once more with 100 ml of water
  3. dry with materialthe organic layer dried with sodium sulfate
  4. customthe solvent removed

Sources & evidence

ORD record
ord-d0f67f0815cf426686312db1c69c13b8
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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