Sodium Iodide → HCID 86598320, compound

Participants

Reaction Steps

Trimethylsilyl chloride (0.25 ml, 1.97 mmol) was added dropwise to a solution of 3,5-dichloro-N-trifluoroacetyl-O-[2-[3-(4-methoxyphenoxy)phenyl]ethyl]-L-tyrosine methyl ester (190 mg, 0.324 mmol) and sodium iodide (292 mg, 1.95 mmol) in acetonitrile (3 ml) at room temperature. The mixture was stirred under argon atmosphere at room temperature for 22 hrs. and then heated under reflux for 9 hrs. The reaction mixture was poured into water (30 ml) and 10% aqueous sodium thiosulfate (20 ml) was added thereto. The mixture was extracted with ethyl acetate and the extract was washed with brine and then dried. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=3) to give 3,5-dichloro-N-trifluoroacetyl-O-[2-[3-(4-hydroxyphenoxy)-phenyl]ethyl]-L-tyrosine methyl ester (120 mg, 65%) as a colorless oil.

Provenance & Evidence