Lithium Hydroxide → HCID 11211862, compound

Participants

Reaction Steps

Methyl ester 6.1 (53 mg) was stirred with 1N LiOH (2 ml) in 5 ml of MeOH/THF (4:1) over 18 h, concentrated, and partitioned between Et2O and H2O. The organic phase was extracted with 0.1 N NaOH (2×), and the combined aqueous extracts were acidified with conc. HCl and extracted with EtOAc (3×). The organic extracts were washed with H2O, brine, and dried (Na2SO4). The residue after concentration was triturated with hexanes/Et2O (10:1) to afford acid 6.2, 39 mg (100%). HRMS (ESI) calc'd for C25H29N2O3 405.2100, found 405.2198 (MH+); MS (ESI); 1H NMR (300 MHz, CDCl3) δ 7.48–7.34 (m, 5H), 7.27 (d, J=7.0, 2H), 7.06 (d, J=8.7, 2H), 6.01 (s, 1H), 5.13 (s, 2H), 4.06–3.98 (m, 1H), 3.02–2.97 (m, 2H), 2.85–2.81 (m, 2H), 1.91–1.83 (m, 6H), 1.26 (br s, 4H).

Provenance & Evidence