Phosgene → {2'-[3-(4-Chloro-benzyl)-1-ethyl-ureidomethyl]-4'-fluoro-6-methoxy-biphenyl-3-yl}-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

(2′-Ethylaminomethyl-4′-fluoro-6-methoxy-biphenyl-3-yl)-acetic acid ethyl ester (0.172 g, 0.5 mmol) and diisopropylethylamine (0.43 mL, 2.5 mmol) were combined in CH2Cl2 (2.5 mL) and cooled to 0° C. Phosgene (20% in toluene; 0.40 mL, 0.75 mmol) was added, and the mixture was stirred for 1 hour. 4-Chlorobenzylamine (0.012 mL, 1.0 mmol) was added, and the reaction was stirred for 1 hour. The mixture was diluted with CH2Cl2 and washed with H2O. The organic layer was dried, filtered, and concentrated, and the residue was purified by preparative HPLC to give {2′-[3-(4-chloro-benzyl)-1-ethyl-ureidomethyl]-4′-fluoro-6-methoxy-biphenyl-3-yl}-acetic acid ethyl ester. The ethyl ester was hydrolyzed with LiOH in THF at room temperature to provide the title compound.

Provenance & Evidence