Hydrochloric Acid → o-(4-Hydroxyphenyl)-3,5-diiodo-l-tyrosine methyl ester

Participants

Reaction Conditions

Reaction Steps

A 6 M solution of HCl in MeOH (8 mL; 48 mmol) was added to a suspension of O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine (2.12 g; 5 mmol) (prepared according to: Chalmers J. R., Dickson G. T., Elks J. and Hems D. A., “The Synthesis of Thyroxine and Related Substances”, Part V., J. Chem. Soc., 3424-3433, 1949) in MeOH (12 mL). The resulting solution was left under stirring for 4 days at 20° C. Then an NaHCO3 aqueous saturated solution was added until pH 7, to obtain a precipitate which was filtered. After concentration of the solution, a second amount of precipitate was obtained. The two samples were combined and dried (50° C.; 1.3 kPa), to, give the desired product (2 g; 3.7 mmol). Yield 87%.

Provenance & Evidence