Triphenylphosphine → Methyl N-isobutyryl-O-{2-[4-(methoxymethyl)phenyl]ethyl}tyrosinate

Participants

Reaction Steps

2-[4-(Methoxymethyl)phenyl]ethanol (0.6 g, 3.61 mmol) and methyl N-isobutyryltyrosinate (1.15 g, 4.34 mmol) were mixed in dichloromethane (20 ml, dry). 1,1′-(Azodicarbonyl)dipiperidine (1.1 g, 4.36 mmol) and triphenylphosphine (1.14 g, 4.35 mmol) were then added respectively. The mixture was stirred at room temperature overnight and filtered. The filtrate was evaporated in vacuum to dry. Column chromatography of the residue on silica gel using ethyl acetate/heptane (gradient 5:95 to 50:50) as eluant gave 0.71 g desired product, yield 48%.

Provenance & Evidence