Da. Smith et al., NITRILOTRIACETAMIDE - SYNTHESIS IN CONCENTRATED SULFURIC-ACID AND STABILITY IN WATER, Synthetic communications, 25(24), 1995, pp. 4123-4132
Acid hydrolysis of N(CH2CN)(3) leads either nitrilotriacetamide, 1, an
d/or 3,5-dioxopiperazineacetamide, 4, in quantitative yield. 1 slowly
and cleanly converts to 3,5-dioxopiperazineacetic acid, 5, in water, a
lthough ammonium salts prevent this reaction.