Diisopropylethylamine → HCID 178446064, compound

Participants

Reaction Steps

100 mg (0.256 mmol) of (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide and 0.052 ml of Hunig base in 2 ml of acetonitrile were treated with 92 mg of (S)-α-(diphenylacetoxy)hydrocinnamic acid and 113 mg of BOP in 2 ml of acetonitrile and stirred at room temperature for 12 hours. The reaction solution was then poured onto 1N hydrochloric acid/ice, extracted with ethyl acetate, the organic phase was washed with sodium carbonate solution, dried over sodium sulfate and, finally, the solvent was removed under reduced pressure. The residue was chromatographed on silica gel with a 10:1 mixture of methylene chloride and methanol, to obtain 130 mg of (S)-α-[[(S)-1-[[(1S,2S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl dibenzylacetate in the form of an amorphous solid. MS 733 (M+H)+.

Provenance & Evidence