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

Participants

Reaction Steps

Synthesis Fmoc-3-nitro-O-(dibenzylphosphoryl)tyrosine allyl ester 3 (3.15 g, 4.2 mmol) was dissolved in dry THF (20 mL), after which N-methylaniline (1.40 mL, 12.9 mmol) and tetrakis triphenylphosphine palladium (254 mg, 0.22 mmol) were added. After stirring for 2 h at room temperature under a N2-atmosphere in the dark, EtOAc (50 mL) and 1M KHSO4 (50 mL) were added. After drying on Na2SO4 and column chromatography (5% MeOH in DCM), the product (2.72 g, 91%) was obtained as a light yellow foam.

Provenance & Evidence