Triphenylphosphine → N-(Triphenylmethyl)-O-[4-[6-benzyloxy-3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophen-2-yl]phenyl]-L-serine methyl ester

Participants

Reaction Steps

To a stirring solution of 6-benzyloxy-2-(4-hydroxyphenyl)-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophene (359 mg, 0.67 mmol), triphenylphosphine (300 mg) and N-trityl-L-serine methyl ester (392 mg) in THF (6 mL) at 0° C. was added diethyl azodicarboxylate (0.18 mL) over 5 min. The mixture was stirred at ambient temperature under argon for 24 h before concentration under reduced pressure. Chromatography with EtOAc followed by Et3N:MeOH:EtOAc (5:5:90) afforded the product (165 mg, 19%).

Provenance & Evidence