Butyl isocyanate → HCID 178449584, compound

Participants

Reaction Steps

0.100 g (0.145 mmol) of t-butyl [(S)-α-[[(S)-1-[[(1S,2S,4S)-6-amino-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate hydrochloride in 1 ml of ethanol is treated with 0.05 ml (0.25 mmol) of Hunig base, cooled to 0° and treated with 0.018 ml (0.16 mmol) of butyl isocyanate in 1 ml of ethanol. Then, the reaction mixture is stirred at room temperature for 2 hours and subsequently evaporated under reduced pressure. Chromatography of the residue on 5 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent yields 0.063 g of t-butyl [(S)-α-[[(S)-1-[[(1S,2S,4S)-6-(3-butylureido)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropylhexyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate as an amorphous solid, MS: 754 (M+H)+.

Provenance & Evidence