1,2-Dimethoxyethane → (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

Benzyl Boc-4-iodophenylalanine (1 eq.), arylboronic acid (1.5 eq.), sodium carbonate (2 eq.), palladium acetate (0.05 eq.) and tri ortho-tolylphosphine (0.1 eq.) was added to a degassed mixture of dimethoxyethane (6 ml/mmol amino acid) and water (1 ml/mmol amino acid). The reaction mixture was kept under argon and heated to 80° C. for 4-6 h. After cooling to room temperature, the mixture was filtered through a short pad of silica gel and sodium carbonate. The filter cake was further washed with ethyl acetate and combined with the other fraction before the solvents were removed under reduced pressure. The products were purified using flash chromatography using mixtures of ethyl acetate and n-hexane as eluent.

Provenance & Evidence