Methyl iodide → HCID 68867449, compound

Participants

Reaction Steps

A solution of a diasteriomeric mixture of 2-methyl-3-{4-[2-(1-naphthalen-2-ylmethyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-phenoxy-propionic acid ethyl ester (0.275 g, 0.498 mmol) in DMF (7 mL) is treated with NaH (60% oil suspension, 0.030 g, 0.750 mmol) and stirred at room temperature under N2 for 30 minutes. The reaction is cooled to 0° C. and treated with iodomethane (0.141 g, 0.996 mmol) and then warmed to room temperature and stirred for 3 hours. The reaction is quenched with 1 N HCl (5 mL) and worked up extractively with Et2O and water. The organic layer is dried and the solvent removed in vacuo to afford crude product that is purified by flash chromatography using 4:1 hexanes:acetone to afford 0.268 g (95%) 2-methyl-3-{4-[2-(3-methyl-1-naphthalen-2-ylmethyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-phenoxy-propionic acid ethyl ester. The diasteriomeric products are separated by chiral HPLC (8×32 cm Chiralpak AD, 100% IPA, 350 mL/min, 270 nm, to give products in>99% de 1H NMR. Rf=0.35 (1:1 acetone:hexanes). MS (ES+) Calc'd for C35H39N2O5 (M+1) 567. Found m/z 567 (100%).

Provenance & Evidence