Trifluoroacetic acid → (S)-1-[(S)-2-((S)-2-methylamino-propionylamino)-2-(tetrahydro-pyran-4-yl)-acetyl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2-fluoro-6-methyl-phenyl)-amide

Participants

Reaction Steps

In a 50 mL round-bottomed flask, tert-butyl (S)-1-((S)-2-((S)-2-(2-fluoro-6-methylphenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethylamino)-1-oxopropan-2-yl(methyl)carbamate (30 mg, 50.2 μmol, Eq: 1.00) was combined with DCM (3 mL) to give a colorless solution. TFA (1 mL, 13.0 mmol, Eq: 259) was added and the reaction was stirred at rt for 30 min. The reaction mixture was concentrated in vacuo and the residue was treated with saturated aqueous NaHCO3 (10 mL). The resulting mixture was extracted with DCM (2×10 mL), the combined organic layers dried over Na2SO4, and then concentrated in vacuo to give (S)-1-[(S)-2-((S)-2-methylamino-propionylamino)-2-(tetrahydro-pyran-4-yl)-acetyl]-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2-fluoro-6-methyl-phenyl)-amide (13 mg), m/z=498 (M+H).

Provenance & Evidence