Sodium Hydroxide → phenylmethyl {(1S)-1-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylcarbonyl]-2,2-dimethylpropyl}carbamate

Participants

Reaction Steps

A solution of 1,1-dimethylethyl (1S,4S)-5-(3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (2.5 g, 5.5 mmol) in 30 ml TFA/DCM (20%) was stirred at room temperature for 1 h. The reaction mixture was made basic by addition of sodium hydroxide, then extracted with DCM (3×50 mL). The DCM was dried over anhydrous Na2SO4 and concentrated to give the title compound (1.8 g) as a pale brown oil. LCMS (m/z): 346.1 (M+H).

Provenance & Evidence