tert-Butyl isocyanate → 1-[2(S)-Hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[tert-butylaminocarbonyl]-hydrazine

Participants

Reaction Steps

Under a protective gas atmosphere, 100 mg (0.178 mmol) of 1-[2(S)-hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]hydrazine (Example 71E) i)) are dissolved in 0.7 ml of THF and reacted with 19 μl (0.169 mmol) of tert-butyl-isocyanate for 17 h at RT. The reaction mixture is concentrated by evaporation, the residue is dissolved in ethyl acetate and washed with 5% citric acid solution, water and brine, and the inorganic phases are extracted twice with ethyl acetate, dried with Na2SO4 and concentrated by evaporation. Column chromatography (SiO2, ethyl acetate/ethanol 10:1) yields the title compound: TLC Rf (F')=0.16; tRet (V)=15.3 min; FAB-MS (M+H)+ =660.

Provenance & Evidence