Lithium Hydroxide → HCID 11429974, compound

Participants

Reaction Steps

A mixture of methyl ester 4.1 (50 mg, 0.112 mmol) and 1N LiOH (2 ml) in 3 ml of MeOH/THF (1:2) was stirred at rt for 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 combined organic extracts were washed with H2O, brine, and dried (Na2SO4) before being concentrated to afford 47 mg (100%) of 4.2. HRMS (ESI) calc'd for C26H29N2O3 417.2178, found 417.2174 (MH+); 1H NMR (300 MHz, CDCl3) δ 7.81 (d, J=1.1, 1H), 7.49–7.36 (m, 5H), 7.30 (d, J=8.7, 2H), 7.07 (d, J=8.7, 2H), 6.45 (s, 1H), 5.14 (s, 2H), 4.14–4.07 (m, 1H), 2.26 (d, J=1.5, 3H), 2.07–2.00 (m, 2H), 1.95–1.84 (m, 4H), 1.36–1.22 (m, 4H).

Provenance & Evidence