tert-butyl N-(2-fluoro-5-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methyl-beta-alaninate → N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methyl-beta-alanine

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Reaction Steps

tert-butyl N-(2-fluoro-5-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methyl-beta-alaninate obtained in step 1 was dissolved in HCl in dioxane (4M, 10 mL), stirred at RT for 30 h. After this time, solvents were removed under vacuum, residue was triturated with Et2O and filtered to give the title compound as an off-white powder. 1H NMR (DMSO-d6, 300 MHz) δ 12.74 (bs, 1H), 10.38 (bs, 1H), 8.36-8.33 (m, 1H), 8.23-8.20 (m, 1H), 8.18-8.15 (m, 1H), 7.87-7.84 (m, 1H), 7.72 (t, J=7.8 Hz, 1H), 7.44 (d, J=7.9 Hz, 1H), 7.37-7.28 (m, 3H), 7.15-7.13 (m, 1H), 4.48 (bs, 2H), 4.23 (d, J=12.7 Hz, 1H), 4.16 (d, J=12.7 Hz, 1H), 3.25 (s, 3H), 2.89-2.84 (m, 2H), 2.70 (s, 3H), 2.03 (s, 3H). LC/MS (Method B): 472.4 (M+H)+. HPLC (Method A) Rt 4.53 min (purity: 97.4%).

Provenance & Evidence