Sodium Iodide → tert-butyl methyl((S)-1-((2S,3S)-2-methyl-5-((3-methylquinolin-4-yl)methyl)-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl)carbamate

Participants

Reaction Steps

To a rt suspension of (3-methylquinolin-4-yl)methanol (90 mg, 520 μmol) in CH2Cl2 (5.2 ml) was added triethylamine (145 μl, 1.04 mmol), followed by methanesulfonyl chloride (48.4 μl, 624 μmol), dropwise. The reaction was stirred at rt for 2 h, then diluted with CH2Cl2, washed with H2O and sat. aq. NaCl, dried over Na2SO4, filtered, and concentrated. This material was mixed with tert-butyl methyl((S)-1-((2S,3S)-2-methyl-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl)carbamate (167 mg, 336 μmol), cesium carbonate (142 mg, 437 μmol), and sodium iodide (65.5 mg, 437 μmol) in DMF (841 μl). The reaction was stirred at rt for 3.5 days, then diluted with EtOAc, washed with H2O and sat. aq. NaCl, dried over Na2SO4, filtered, and concentrated. The crude material was purified by flash chromatography to provide tert-butyl methyl((S)-1-((2S,3S)-2-methyl-5-((3-methylquinolin-4-yl)methyl)-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl)carbamate (142 mg, 65%) as a white solid. MS m/z 652 (MH)+.

Provenance & Evidence