Lithium hydroxide, monohydrate → HCID 69414852, compound

Participants

Reaction Steps

A solution of 4-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-benzoic acid methyl ester (0.20 g, 0.34 mmol) in tetrahydrofuran (7.5 mL) and H2O (2.5 mL) at ambient temperature was treated with LiOH.H2O (0.029 g, 0.68 mmol). The mixture was stirred overnight at ambient temperature. The mixture was then treated with additional LiOH.H2O (0.058 g, 1.37 mmol) and heated at 50° C. overnight. The reaction was cooled to 0° C. and was quenched with H2O (5 mL). The mixture was the acidified to a pH=2 with 1 N HCl (aq.). The mixture was then extracted three times with EtOAc, dried, filtered and concentrated in-vacuo to afford the carboxylic acid product. The acid was purified via reverse-phase HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm) to yield the title compound, 0.140 g (72%); MS (ESI) m/e 569 [M+H]+.

Provenance & Evidence