Diethyl Ether → HCID 11188844, compound

Participants

Reaction Steps

To a solution of ester 2.3 (55 mg, 0.132 mmol) in 4.5 ml of THF/MeOH (8:1) was added 1N LiOH (2 ml), and the mixture was stirred for 24 h at rt. Concentration to remove solvent gave a residue that was taken Et2O and extracted with 0.1 N NaOH and H2O (2×). The combined aqueous extracts were acidified with concentrated HCl and extracted with EtOAc (3×). The combined organic extracts were washed with H2O, brine, dried (Na2SO4). The crude product was triturated with hexanes to afford 45.8 mg (86%) of acid 2.4. HRMS (ESI) calc'd for C25H27N2O3 403.1943; found 403.2019 (MH+); 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=16.1, 1H), 7.49–7.34 (m, 5H), 7.28 (d, J=8.8, 2H), 7.07 (d, J=8.8, 2H), 6.46 (s, 1H), 6.38 (d, J=15.7, 1H), 5.13 (s, 2H), 4.14–4.04 (m, 1H), 2.03–1.82 (m, 6H), 1.28–1.24 (m, 4H).

Provenance & Evidence