Methanol → tert-butyl (2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxopentan-3-ylcarbamate

Participants

Reaction Steps

Under an atmosphere of argon, (2S,3S)-3-(tert-butoxycarbonylamino)-1-(cyclopropylamino)-1-oxopentan-2-yl acetate (1.09 g, 3.47 mmol, Eq: 1.00) and NaOH 1N in H2O (5.2 ml, 5.2 mmol, Eq: 1.5) were combined with methanol (10 ml) to give a colorless solution. The reaction was stirred for 2 h at RT. The reaction mixture was poured into 25 mL H2O and extracted with ethyl acetate (2×50 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The title compound was obtained as a light brown solid (540 mg, 57.2%, MS (m/e)=273.4 [M+H+]).

Provenance & Evidence