Dimethylformamide → HCID 89690029, compound

Participants

Reaction Steps

Add thionyl chloride (8.22 mL, 113 mmol) dropwise to a solution of 3-[3-[5-benzyloxy-2-ethyl-4-(4-fluorophenyl)phenoxy]propoxy]-2-propyl-benzoic acid (50.0 g, 92 mmol) and DMF (2.5 mL, 32 mmol) in THF (250 mL). Stir for 1 h and then add the reaction to a solution of ammonium hydroxide (102.5 mL, 1.52 mol) at 0-5° C. Add MeOH (250 mL) and water (500 mL) in a dropwise fashion. Concentrate to about one half the volume in vacuo and stir the resulting suspension 30 min at 0-5° C. Filter the suspension on a glass frit and dry the resulting solids under vacuum to provide the title compound (50.3 g, quantitative) as an off-white solid. ES/MS m/z 542 (M+1).

Provenance & Evidence