tert-Butyl (3-aminopropyl)carbamate → benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-[[4-[[3-[(2-methylpropan-2-yl)oxycarbonylamino]propylamino]methyl]triazol-2-yl]methyl]-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylate

Participants

Reaction Steps

To a solution of benzhydryl 1-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((2R,3S)-2-((4-formyl-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylate (370 mg, 0.52 mmol) in DCE (4 mL) at 0° C. was added tert-butyl(3-aminopropyl)carbamate (180 mg, 1.04 mmol) and sodium triacetoxyhydroborate (165 mg, 0.78 mmol) sequentially. After stirring at rt for 16 h, the reaction mixture was diluted with DCM, washed with saturated NaHCO3 (aq), brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (assumed quantitative). The crude residue was used as such in the following step. LCMS: Rt=0.99 min, m/z=873.2 (M+1). Method 2m_acidic.

Provenance & Evidence