p-Toluenesulfonic acid monohydrate → benzyl 3-[(E)-C-(3,3-dimethoxypropyl)-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbonimidoyl]azetidine-1-carboxylate

Participants

Reaction Steps

A solution of benzyl 3-(4,4-dimethoxybutanoyl)azetidine-1-carboxylate (1.91 g, 5.94 mmol) in CH2Cl2 (30 mL) was treated with Pert-butylcarbazate (824 mg, 6.24 mmol) followed by para-toluensulfonic acid monohydrate (170 mg, 0.89 mmol). The reaction was stirred at rt for 16 h. The mixture was washed with H2O (25 mL), saturated aqueous NaHCO3 (25 mL), and brine. The organic phase was dried (Na2SO4), filtered and concentrated to afford 2.47 (95%) of the desired product. ES-MS m/z 458.47 [M+Na]+, HPLC RT (min) 3.32.

Provenance & Evidence