Triethylsilane → HCID 68867189, compound

Participants

Reaction Steps

A solution of 3-(4-{2-[3-(4-methoxy-benzyl)-1-naphthalen-2-ylmethyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (1.54 g, 2.29 mmol) and triethylsilane (0.53 g, 4.56 mmol) in trifluroacetic acid (40 mL) is stirred at room temperature under N2 for 4 hours. The reaction mixture is diluted with water and extracted with EtOAc. The organic layer is dried and the solvent removed in vacuo to afford crude product that is purified by flash chromatography using 3:1 then 1:1 hexanes:acetone to afford 1.25 g (100%) 2-methyl-3-{4-[2-(1-naphthalen-2-ylmethyl-2-oxo-imidazolidin-4-yl]-ethoxy)-phenyl}-2-phenoxy-propionic acid ethyl ester. The diastereomeric mixture could be separated by chiral HPLC (2:3 IPA:heptane mobile phase, 14 mL/min, 225 nm) to afford >99% de 2-methyl-3-{4-[2-(1-naphthalen-2-ylmethyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-phenoxy-propionic acid ethyl esters. Rf=0.19 (1:1 acetone:hexanes). 1H NMR. MS (ES+) Calc'd for C34H37N2O5 (M+1) 553. Found m/z 553 (100%).

Provenance & Evidence