Aniline → HCID 131735249, compound

Participants

Reaction Steps

In a 50 mL round-bottomed flask, 1-((S)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (300 mg, 744 μmol, Eq: 1.00) and HATU (339 mg, 892 μmol, Eq: 1.2) were combined with DMF (7 mL) to give a colorless solution. Triethylamine (124 μL, 892 μmol, Eq: 1.2) and aniline (83 mg, 892 μmol, Eq: 1.2) were added and the reaction was stirred at rt overnight. The reaction mixture was poured into water (10 mL) and extracted with EtOAc (2×25 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 24 g, 5% to 25% EtOAc in hexanes) to give tert-butyl (R)-(1S)-1-cyclohexyl-2-oxo-2-(2-(phenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)ethylcarbamate (eluted first, 160 mg) and tert-butyl (S)-(1S)-1-cyclohexyl-2-oxo-2-(2-(phenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)ethylcarbamate (eluted second, 130 mg), m/z=479 (M+H).

Provenance & Evidence