Benzyl acetoacetate → (E)-3-[4-(tert-Butoxycarbonylamino-methyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl Ester

Participants

Reaction Steps

To a solution of (4-amino-3-iodo-benzyl)-carbamic acid tert-butyl ester (3.5 g, 10 mmol) and benzyl acetoacetate (1.92 g, 10 mmol) in benzene (80 mL) was added p-toluenesulfonic acid (95 mg, 0.5 mmol). The mixture was heated at reflux overnight using a Dean Stark condenser. The mixture was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give 5.25 g (99%) of crude desired product as a light brown oil: MS(APCI+): m/z 523.1 (MH+). The compound was taken to Step D without further purification.

Provenance & Evidence