Resolution of dl-thyroxine

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Abstract
Thyroxine is designated as 3, 5, 3[image], 5[image] tet-raiodothyronine. 3, 5 dl-diiodothyronine was converted into the formyl derivative by warming on the water bath with anhydrous formic acid. The crystalline residue was extracted with warm absolute alcohol and poured into excess of hot water. On slow cooling, the compound crystallized out. Attempts to resolve this through alkaloidal salts failed, but success followed formation of a salt with 1-phenylethylamine. The insoluble fraction could not be obtained optically pure, but the soluble fraction, after recrystallization, had [image]+23.8. Upon decomposition of the salt and hydrolysis with HBr, l-diiodothyronine was obtained, [image] [long dash]1.3. Iodination gave l-thyroxine. The corresponding dextro compound was also made and found to be 1/3 as active physiologically.

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