Acetic Acid → tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate

Participants

Reaction Steps

(2S,5R)-6-(benzyloxy)-4-(2-nitroethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (Intermediate 226, 0.420 g, 1.21 mmol) was taken up in ethanol (absolute, 99.5%) (20 mL), and zinc dust (1.983 g, 30.32 mmol) was added followed by acetic acid (2.78 mL, 48.51 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. DIPEA (2.118 mL, 12.13 mmol) was added followed by BOC-anhydride (0.845 mL, 3.64 mmol). The reaction mixture was stirred for 2 hours, then diluted with DCM, washed with saturated bicarbonate and concentrated to dryness. Flash chromatography, 0-10% MeOH/DCM, afforded the title compound as a clear oil (0.31 g, 61%).

Provenance & Evidence