N-(tert-butoxycarbonyl)glycine → tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

Participants

Reaction Steps

8.75 g (50 mmol) of BOC-glycine dissolved in 150 ml DCM and 6.95 ml (50 mmol) of TEA was added to the solution, and stirred. 17.42 g (50 mmol) BOP reagent (Richelieu Biotechnologies, QC, Canada) was added, followed a few minutes later with O,N-dimethylhydroxylamine hydrochloride (5.6 g, 55 mmol) and TEA (7.67 g, 55 mmol). The reaction was complete in 60 min, and the result was verified by TLC monitoring. A small amount of TEA was used to neutralize the mixture (adjust the pH to above 7.0) in order to allow the reaction go to completion. The mixture was diluted to 500 ml with DCM. The solution was washed in turn with 3N HCl (3×100 ml), saturated NaHCO3 (3×100 ml), and brine (3×100 ml). The DCM layer was dried over MgSO4 and concentrated to obtain the crude product. Recrystallization from water afforded 5.85 g Nα -(BOC)-glycine N-methoxy-N-methylamide (m.p. 92°-95° C.). This product was dried thoroughly in vacuo over P2O5 before use in the following reaction.

Provenance & Evidence