1,4-Dioxane → HCID 70507138, compound

Participants

Reaction Steps

2-Naphthylmethyl 1-hydroxy-2-methyl-6-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapenam-3-carboxylate (36 mg., 0.056 mmole) was dissolved in 2 ml. of dioxane. Water (1 ml.), sodium bicarbonate (4.7 mg., 0.056 mmole) and hydrogenation catalyst (36 mg. of 10% palladium on carbon) were added and the mixture was hydrogenated at 50 psig and room temperature for 30 minutes. Monitoring by tlc (9:1 acetone:water and 90:10:2 chloroform:ethanol:acetic acid) indicated that hydrogenation was incomplete. An additional 36 mg. of 10% palladium on carbon was added and hydrogenation, under the same conditions, resumed for 30 minutes, at which time tlc monitoring indicated reaction was complete. Catalyst was recovered by filtration and the filtrate freeze dried to yield sodium 1-hydroxy-2-methyl-6-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapenam-3-carboxylate [10 mg., 34%; Rf 0.3 (9:1 acetone:water; Rf 0.3 (90:10:2 chloroform:ethanol:acetic acid); ir (nujol mull) 1770, 1750, 1710 cm-1 ].

Provenance & Evidence