Sodium Hydroxide → HCID 86700874, compound

Participants

Reaction Steps

To a solution of methyl 2-(4-(4′-((5-(tert-butyl)-1,3,4-oxadiazol-2-yl)amino)-[1,1′-biphenyl]-4-yl)-7-oxabicyclo[2.2.1]heptan-1-yl)acetate (110 mg, 0.24 mmol) in THF (4 mL) and Methanol (1 mL) was added 1N NaOH (0.72 mL, 0.72 mmol) and the reaction was let stir at rt for 2 hr. The resulting yellow reaction mixture was partially concentrated by rotary evaporation in vacuo (rt water bath). The yellow solution was diluted with MeOH, filtered and purified on preparative HPLC (10-50% MeCN:5 mM NH4OH) to afford 52 mg (49%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.36 (s, 9H), 1.63-1.82 (m, 4H), 1.90-2.02 (m, 2H), 2.08-2.21 (m, 2H), 2.79 (s, 2H), 7.42 (d, J=8.3 Hz, 2H), 7.56-7.70 (m, 6H), 10.51 (br. s., 1H). ESI-MS m/z: 448.1 [M+H]+, retention time 1.08 min (condition E). HR/MS [M+H]+: found 448.2236. calc. 448.2218. RT: 2.27 (Condition L).

Provenance & Evidence