4-Methoxy-2-nitrophenyl isothiocyanate → (1,1-dimethyl ethyl) N-[[(2-amino-4-methoxyphenyl)amino]thioxomethyl]-O-(4-ethoxy-4-oxobutyl)-L-tyrosinate

Participants

Reaction Steps

The aminoester 4-2 (350 mg, 1 mmole) in 20 ml of THF is mixed with 4-methoxy-2-nitrophenyl isothiocyanate (210 mg, 1 mmole), followed by agitating for 1 hour at ambient temperature, evaporating under reduced pressure, then adding SnCl2 (380 mg then 190 mg, 3 mmoles) in 10 ml of DMF and agitating for 4 hours at ambient temperature. After evaporating under reduced pressure and taking up in a water/NaHCO3/AcOEt mixture, decanting, drying the organic phase and evaporating under reduced pressure, 530 mg of crude product is obtained.

Provenance & Evidence