N-Methylaniline → Fmoc-3-azido-O-(dibenzylphosphoryl)tyrosine

Participants

Reaction Steps

Fmoc-3-azido-O-(dibenzylphosphoryl)tyrosine allyl ester 11 (969 mg, 1.30 mmol) was dissolved in dry THF (10 mL), after which N-methylaniline (0.42 mL, 3.9 mmol) and tetrakis triphenylphosphine palladium (75 mg, 0.065 mmol) were added. After stirring for 2 h at room temperature under a N2-atmosphere in the dark, EtOAc (30 mL) and 1M KHSO4 (30 mL) were added. After drying on Na2SO4 and column chromatography (3% MeOH in DCM), the product (386 mg, 42%) was obtained as a white foam.

Provenance & Evidence