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

Participants

Reaction Conditions

Reaction Steps

To a solution of Boc-Gly-OH (4250 g, 24.26 mol), N,O-dimethylhydroxylamine-HCl (2839 g, 29.10 mol) and DMAP (297 g, 2.43 mol) in dichloromethane (36 L), is added triethylamine (5.54 L) at 0° C. over a period of 90 min followed by the addition of EDC hydrochloride (5674 g, 29.60 mol). The mixture is stirred at 0° C. for 1 h then warmed to room temp for 24 h. The reaction mixture is cooled to 0° C. and quenched with 1.0M HCl to pH 3 to 4, stirred at room temp for 20 min, then allowed to stand and separate. The organic phase is washed successively with 1.0M HCl (15 L), water (15.0 L) and brine (8.0 L), dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure to provide the title compound (4985 g; 94% yield) as a white solid.

Provenance & Evidence