benzyl 3-[(E)-C-(3,3-dimethoxypropyl)-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbonimidoyl]azetidine-1-carboxylate → benzyl 3-(1-[(tert-butoxycarbonyl)amino]-1H-pyrrol-2-yl}azetidine-1-carboxylate

Participants

Reaction Steps

A solution of benzyl 3-[(1E)-N-(tert-butoxycarbonyl)-4,4-dimethoxybutanehydrazonoyl]azetidine-1-carboxylate (2.47 g, 5.67 mmol) and AcOH (30 mL) was stirred (40° C.) for 18 h. The mixture was concentrated and the residue was dissolved in EtOAc (75 mL) and washed with saturated, aqueous NaHCO3 (75 mL). The aqueous layer was extracted with EtOAc (2×50 mL) and the combined organic layers were washed with brine, dried (Na2SO4) and concentrated to afford the desired product (2.1 g) which was used without further purification. ES-MS m/z 272.01 [M+H]+, HPLC RT (min) 3.50.

Provenance & Evidence