Diethyl cyanophosphonate → HCID 22849831, compound

Participants

Reaction Steps

220 mg (0.865 mmol) of 1-[(2S,3S)-3-amino-4-cyclohexyl-2-hydroxybutyl]-2-pyrrolidinone and 300 mg (0.618 mmol) of 1-(t-butoxycarbonyl)-N-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamoyl]-L-histidine were dissolved in 5 ml of methylene chloride, cooled to -20° and treated with 0.16 ml of N,N-diisopropylethylamine and 0.12 ml of diethyl cyanophosphonate. Thereupon, the reaction mixture was stirred at room temperature for 19 hours and subsequently poured into a mixture of ice and dilute sodium bicarbonate solution and extracted with methylene chloride. The methylene chloride extracts were dried over magnesium sulfate and evaporated, and the residue was chromatographed on 5 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent, whereby there were obtained 430 g (96%) of (S)-N-[(1S,2S)-1-(cyclohexylmethyl)-2-hydroxy-3-(2-oxo-1-pyrrolidinyl)propyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamamido]-3-t-butoxycarbonylimidazole-4propionamide as a yellow foam which was used directly in the next step.

Provenance & Evidence