Hydrochloric Acid → 4-(4-Fluoro-3,5-diisopropoxybenzamido)benzoic acid

A suspension of methyl 4-(4-fluoro-3,5-diisopropoxybenzamido)benzoate (10) (32 mg, 51% purity, 82 μmol) in THF (1 mL) and 2M LiOH (0.16 mL, 0.33 mmol) was stirred at RT for 20 h, then at 45° C. for 2 h. The mixture was allowed to cool to RT and was acidified by the addition of 1M HCl. The mixture was partitioned between EtOAc (10 mL) and water (10 mL) and the phases were separated. The organic solution was washed with brine (3× mL), then dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by reverse phase HPLC to afford 4-(4-fluoro-3,5-diisopropoxybenzamido)benzoic acid (AAA-119) (8 mg, 38%) as a white solid: m/z 376 [M+H]+ (ES+), 374 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 10.37 (1H, s), 7.93 (2H, d), 7.83 (2H, d), 7.35 (2H, d), 4.73 (2H, sep), 1.32 (12H, d). NB acid proton not visible.

1. waitat 45° C. for 2 h
2. temperatureto cool to RT
3. customThe mixture was partitioned between EtOAc (10 mL) and water (10 mL)
4. customthe phases were separated
5. washThe organic solution was washed with brine (3× mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customThe solvent was removed in vacuo
9. customthe residue was purified by reverse phase HPLC

ORD record

ord-e8b96f9730234de7bc3e3f2e85e978ba

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447028B2