N-Hydroxysuccinimide → HCID 86746027, compound

Participants

Reaction Steps

To a solution of m-(carboxymethoxy)phenyl acetone (6.1 g, 0.029 mole) in N,N-dimethylformamide (56 ml, dried over molecular sieves, 3A) were added under nitrogen at 5° powdered 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 6.1 g, 0.032 mole) and N-hydroxysuccinimide (3.7 g, 0.032 mole). The resulting reaction mixture was then allowed to stir at 5° overnight. The complete formation of N-hydroxysuccinimic ester was observed. To the methyldithioethylamide hydrochloride (4.7 g, 0.029 mole, prepared in D above) in water (20-50 ml) was added triethylamine to adjust the pH to 8.5. Then the N-hydroxysuccinimic ester of m-(carboxymethoxy)phenyl acetone was added dropwise to the methyldithioethylamine solution with the adjustment of pH to 8.5, and the resulting solution was allowed to stir at 5° for 1 hour. Additional reagents, methyldithioethylamine hydrochloride (2 g, 0.0125 mole) and EDCI (3.0 g, 0.0156 mole), were added and the pH of the resulting solution was adjusted to 6.5 and the reaction mixture was allowed to stir at 5° overnight.

Provenance & Evidence