Trifluoroacetic acid → (S)-1-((S)-2-((S)-2-aminopropanamido)-3-methylbutanoyl)-N-phenyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 627046Notes

Reaction equation

HRID 627046 reaction equation
[CH3:1][CH:2]([CH3:37])[C@H:3]([NH:24][C:25](=[O:36])[C@@H:26]([NH:28]C(=O)OC(C)(C)C)[CH3:27])[C:4](=[O:23])[N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7][C@H:6]1[C:14](=[O:22])[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:28][C@@H:26]([CH3:27])[C:25]([NH:24][C@@H:3]([CH:2]([CH3:37])[CH3:1])[C:4]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7][C@H:6]1[C:14]([NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:22])=[O:23])=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735266HCID 131735266, compound

Product 1

HCID 118380538(S)-1-((S)-2-((S)-2-aminopropanamido)-3-methylbutanoyl)-N-phenyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamideYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 mL round-bottomed flask, tert-butyl (S)-1-((S)-3-methyl-1-oxo-1-((S)-2-(phenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)butan-2-ylamino)-1-oxopropan-2-ylcarbamate (75 mg, 147 μmol, Eq: 1.00) was combined with DCM (6 mL) to give a colorless solution. TFA (1.9 mL, 24.9 mmol, Eq: 169) was added. The reaction was stirred for 30 min and then concentrated in vacuo. The residue was taken up in DCM, washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo to give (S)-1-((S)-2-((S)-2-aminopropanamido)-3-methylbutanoyl)-N-phenyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (55 mg) which was used without further purification.

Workup

  1. customto give a colorless solution
  2. concentrationconcentrated in vacuo
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a27f85973954765a9e97517e4038201
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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