Dimethylformamide → 6-Aminohexanoic Acid

Participants

Reaction Steps

An N-hydroxysuccinimidyltricaproamidocyclohexylmethylmaleimide, a compound having the structure of FIG. 14 of the attached drawings where Z has the structure of FIG. 3, Z' has the structure of FIG. 11, n is 3, and C6H10 is 1,4-cyclohexyl, was then produced from a solution of 100 mg N-hydroxysuceinimidyldicaproamidocyclohexylmethylmaleimide in 2 ml dry dimethylformamide, 23.4 mg 6-aminocaproic acid and 40.5 mg dicyelohexylearbodiimide. A nitrogen atmosphere was established in a flask above the N-hydroxysuccinimidyldicaproamidocyclohexylmethylmaleimide solution, and the 6-aminocaproie acid was added to the flask. The reaction mixture was then stirred under nitrogen at room temperature of about 22° for 16 hours, after which time the dieyclohexylcarbodiimide was added to the flask. Stirring at room temperature was continued for an additional 6 hours, after which time dicyclohexylurea which had precipitated was removed from the reaction mixture by filtration, and the dimethylformamide was evaporated under reduced pressure from the filtrate. A tacky solid which remained was purified by flash chromatography on silica gel (10v/v methanol in chloroform), yielding 60 mg of the N-hydroxysuccinimidyltricaproamidocyclohexylmethylmaleimide, a white solid which has the indicated formula.

Provenance & Evidence