Trifluoroacetic acid → 3-(4-Carboxy-2-methoxyphenylmethylthio)-3-[2-(8-phenyloctyl)phenyl]propionic acid

Participants

Reaction Steps

A solution of 0.54 g (1.32 mmol) of tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate and 0.52 gm, (2.64 mmol) of 3-methoxy-4-mercaptomethylbenzoic acid in 10 ml of methylene chloride at 0° was treated dropwise with 20 ml of trifluoroacetic acid. Stirring was continued at 0° for 4 hours and 221 for 1 hour, and all the solvents were thoroughly evaporated. The residue was crystallized first from H2O/MECN (1:4), and then from Me2CO/hexane, and to yield the product, 0.26 gm. nmr (CDCl3 /Me2CO/DMSO): 7.05-7.72(m, 12H), 4.52 (d of d, 1H), 4.83(d, 1H), 4.82(s,3H), 4.68(d.1H), 2.88-3.24(m, 2H), 2.36-2.74 (m, 4H), 1.10-1.75(m,12H).

Provenance & Evidence