Trifluoroacetic acid → HCID 67497386, compound

HRID 1628331Notes

Reaction equation

HRID 1628331 reaction equation
[O:1]=[C:2]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:28]3[CH:29]=[N:30][CH:31]=[N:32][CH:33]=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:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>ClCCl>[F:37][C:36]([F:39])([F:38])[C:34]([OH:40])=[O:35].[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]=[N:32][CH:31]=[N:30][CH:29]=3)[CH:26]=2)[CH2:21][CH2:20]1)=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67497592HCID 67497592, compound

Product 1

HCID 67497386HCID 67497386, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The (S)-tert-butyl 1-oxo-3-phenyl-1-(6-(pyrimidin-5-yl)indolin-1-yl)propan-2-ylcarbamate (64 mg, 144 μmol) was dissolved in dichloromethane (1.0 mL) and TFA (1.0 mL, 13 mmol) was added. The resulting solution was stirred for three hours then concentrated. The residue was taken up in ethyl acetate and filtered and washed with hexanes to give the desired product (S)-2-amino-3-phenyl-1-(6-pyrimidin-5-yl-2,3-dihydro-indol-1-yl)-propan-1-one trifluoroacetate (50 mg, 76% yield) as the mono-trifluoroacetic acid salt. MS ESI (pos.) m/e: 345.1 (M+H).

Workup

  1. concentrationthen concentrated
  2. filtrationfiltered
  3. washwashed with hexanes

Sources & evidence

ORD record
ord-8eced6bd753d43e5b32f04c9f876b200
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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