HCID 67404573, compound → HCID 58005156, compound

Participants

Reaction Steps

Et3N (2.0 eq.), hex-5-enal (1.0 eq.) (obtained from hex-5-en-1-ol via a PCC oxidation and sodium triacetoxyborohydride (1.3 eq.) were sequentially added to a 0.07 M solution of methyl (4R)-1-[(2S)-2-amino-2-cyclohexylacetyl]-4-[(3′-vinylbiphenyl-3-yl)methoxy]-L-prolinate hydrochloride 108 in DCE. The reaction mixture was stirred at RT for 2 h then it was diluted with DCM, saturated aqueous NaHCO3 and extracted. The collected organic layers were washed with brine, dried (Na2SO4) and evaporated under reduced pressure to yield a residue that was purified by flash chromatography (SiO2, PE:EtOAc=7:3) to afford the title compound 109 (67%) as a colourless oil.

Provenance & Evidence