Lithium Hydroxide → HCID 11327046, compound

Participants

Reaction Steps

A mixture of ester 7.3 (68 mg, 0.157 mmol) and 1N LiOH (2 ml) in 6 ml MeOH/THF (1:2) was stirred at rt for 24 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 combined organic extracts were washed with H2O, brine, and dried (Na2SO4) to afford 64 mg (100%) of acid 7.4. HRMS (ESI) calc'd for C25H25N2O3 401.1865, found 401.1855 (M+H+); 1H NMR (300 MHz, CDCl3) δ 7.48–7.37 (m, 5H), 7.26 (d, J=8.8, 2H), 7.08 (d, J=8.8, 2H), 6.51 (s, 1H), 5.13 (s, 2H), 4.15–4.06 (m, 1H), 2.05–1.97 (m, 2H), 1.90–1.87 (m, 4H), 1.28–1.23 (m, 4H).

Provenance & Evidence