Sodium Hydroxide → tert-butyl(2S,3S)-8-cyano-2-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

Participants

Reaction Steps

To a rt solution of tert-butyl(3S,4S)-7-cyano-4-methyl-2-oxo-1,5-bis(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate (0.707 g, 1.31 mmol) in MeOH (13.1 ml) was added 1 M aq. sodium hydroxide (1.44 ml, 1.44 mmol), dropwise. The reaction was stirred for 30 min, 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(2S,3S)-8-cyano-2-methyl-4-oxo-1-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate (289 mg, 52%) as a white solid. MS m/z 451 (MNa)+.

Provenance & Evidence