Hydrochloric Acid → N-acetyl-L-thyroxine N-(5-carboxypentyl)-carboxamide

Beteiligte Stoffe

Reaktionsschritte

N-acetyl-L-thyroxine (Anal. Biochem., 33 (1970) 67) (1.0 g, 1.22 mmole) and N-hydroxysuccinimide (0.148 g, 1.28 mmole) are dissolved in 2 ml of dimethylformamide and 3 ml of tetrahydrofuran. Dicychlohexylcarbodiimide (0.264 g=1.28 mmole) is then added all at once and the reaction mixture stirred at room temperature for 4 hours. The dicyclohexylurea is removed by filtration and to the filtrate is added a solution of 6-aminocaproic acid (160 mg, 1.22 mmole) and sodium bicarbonate (204 mg, 2.44 mmole) in 1 ml of water. After stirring 2 hours the reaction mixture is acidified to pH 3 with 2 N HCl and extracted with methylene chloride. The organic extract is dried over magnesium sulfate and evaporated to the crude amide. Purification of the product is achieved by dissolving the crude material in methylene chloride containing a trace of methanol and precipitating the product with ether/hexane (75:25). The procedure is repeated two times to give 223 mg (23%) of pure product. It shows a single spot on TLC in 8% methanol in chloroform. The compound has the formula C22H24N2O6I4 and the following structure ##STR3##

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