Hydrochloric Acid → Thyroxine N-iodoacetamide

Participants

Reaction Steps

78 mg (0.1 mmole) of L-thyroxine was dissolved in 1.0 ml of methanol on addition of 34 mls (0.2 mmole) of 6N NaOH and sonication in a bath sonicator. 48 mg of iodoacetic acid N-hydroxysuccinimide ester was added and the mixture vortexed. 8.5 mls of 6N NaOH was added and the mixture vortexed. TLC (chloroform:methanol:acetic acid 50:6:2 on silica gel) indicated complete reaction. 50 mls of 6N HCl was added and then 4 mls of water and formed a precipitate. The precipitate was collected by centrifugation and washed with 1 ml of methanol and 4 mls of water. After centrifugation the pellet was dried under vacuum to 82 mg of an off-white solid.

Provenance & Evidence