Lithium Hydroxide → {[3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-4-fluoro-benzoyl]-methyl-amino}-acetic acid

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Reaction Steps

{[3-(4′,5′-Difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-4-fluoro-benzoyl]-methyl-amino}-acetic acid ethyl ester (0.29 g, 0.59 mmol) was dissolved in THF (25 mL) and lithium hydroxide solution (0.5N, 2 mL) was added. The mixture was stirred at room temperature for 2 hrs. Solvents were evaporated and the residue was treated with dilute hydrochloric acid and ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. Solvent was evaporated and the residue was dissolved in acetonitrile (1 mL) and diluted with water (8 mL). The mixture was lyophilized to give a fluffy solid as {[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-4-fluoro-benzoyl]-methyl-amino}-acetic acid (0.26 g, 96%). HRMS (ES) calculated for C24H20F3NO5, 482.1186; found m/z 482.1185 [M+Na]+; 1H-NMR (DMSO-d6) δ ppm 12.86 (br s, 1H), 7.29-7.69 (m, 6H), 7.24 (dd, J=13.0, 7.2 Hz, 1H), 7.08 (d, J=8.5 Hz, 2H), 5.19 and 5.23 (s, 2H, rotamer), 3.97 and 4.14 (s, 2H, rotamer), 3.76 (s, 3H), 2.94 and 2.95 (s, 3H, rotamer).

Provenance & Evidence