3',5'-Diiodo-L-tyrosine → tert-butyl (2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoate

Participants

Reaction Steps

A solution of 5.0 g of 3,5-diiodo-L-tyrosine and 0.95 mL of 70% aqueous HClO4 in 155 mL of tert-butyl acetate was stirred at RT under nitrogen for 4 days. The solution was neutralized by addition of 150 mL of 5% aqueous NaHCO3 and the mixture was subjected to rotary evaporation to remove tert-butyl acetate. An off-white precipitate resulted which was collected by filtration and dried in vacuo. The crude product was subjected to flash chromatography on silica gel (97:3 CH2Cl2:MeOH) to afford 4.2 g (75%) of tert-butyl 3,5-diiodo-L-tyrosinate as a white powder, m.p. 165-168° C.

Provenance & Evidence