(R)-5-(Oxiran-2-ylmethoxy)quinoline → 3-{4-[2-(R)-Hydroxy-3-(quinolin-5-yloxy)-propyl]-piperazin-1-yl}-3-oxopropionic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Participants

Reaction Steps

3-(Piperazin-1-yl)-3-oxopropionic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (38) (209.5 mg; 0.497 mmol) is dissolved in ethanol (12 mL) at ambient temperature. (R)-5-Oxiranylmethoxy-quinoline (2) (100.0 mg; 0.497 mmol) is added, then the mixture is refluxed for 15 hours. After cooling to ambient temperature, the solution is concentrated in vacuo at 40° C. The residue is purified via silica gel chromatography with gradient elution (neat ethyl acetate, then 50%→100% acetone in hexanes, then 5% ethanol in acetone) affording the desired product as a solid. ESMS: MH− 623.4

Provenance & Evidence