Triethylamine → 5-Amino-2,10-dimethyl-4,8-dioxo-5-vinyl-3,9-diazaundecanedioic acid

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Reaction Conditions

Reaction Steps

To 2-(benzyloxycarbonyl)amino-2-vinylglutaric acid (305 mg, 1 mM) in methylene chloride (15 ml) is added triethylamine (205 mg, 2 mM) followed by ethyl chloroformate (218 mg, 2 mM). The solution is stirred for one hour at 25° C., then alanine methyl ester (206 mg, 2 mM) in methylene chloride (5 ml) is added. This solution is kept overnight at 25° C., washed with water, dried and evaporated to dryness. The residue is treated with 5 ml of a 40% (w/w) solution of hydrogen bromide in dioxane at 25° C. for 30 minutes. Ether (50 ml) is then added and the precipitate collected. This is then treated with 20 ml of a 1 N sodium hydroxide solution overnight at 25° C., the pH adjusted to 6.5, and applied to an Amberlite 120 H+ resin. Elution with 2 N ammonium hydroxide afforded 5-amino-2,10-dimethyl-4,8-dioxo-5-vinyl-3,9-diazaundecanedioic acid.

Provenance & Evidence