Hydrochloric Acid → tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

Participants

Reaction Steps

To a mixture of N-Boc-glycine 44 (10.0 g, 57.1 mmol), N,O-dimethylhydroxylamine hydrochloride (6.68 g, 68.5 mmol), EDCI (13.1 g, 68.5 mmol), and HOBt (9.26 g, 68.5 mmol) in CH2Cl2 (200 mL) was added NMM (31.4 mL, 285 mmol). The resulting mixture was stirred at room temperature for 15 h. The reaction mixture was poured into 1.0 M HCl solution, and extracted with EtOAc. The organic phase was washed with a saturated NaHCO3 solution and brine, and then dried over anhydrous MgSO4. After evaporation of solvent, the residue was triturated with hexanes (100 mL) to provide the Weinreb amide 45 (10.2 g, 82%) as white solid.

Provenance & Evidence