Hydrochloric Acid → HCID 131726278, compound

Participants

Reaction Steps

A stirred mixture of Example 41 (19.7 mg, 34 μmol), methoxylamine.HCl (17 mg, 204 μmol), NaOAc (17 mg, 204 μmol), and MeOH (2 mL) was heated at 50° C. for 24 h. The solvent was removed under vacuum and the residue was dissolved in EtOAc (500 mL). The organic mixture was washed with satd NaHCO3 (3×100 mL), water (200 mL), and brine (200 mL), dried over Na2SO4, filtered, and evaporated. The residue was lyophilized from CH3CN/H2O/TFA give the title compound as a mixture of (E) and (Z) isomers (26.9 mg, 95%): 1H NMR (500 MHz, CDCl3) δ 11.03 (s, 1H), 7.97–7.86 (m, 3H), 7.83–7.76 (m, 1H), 7.70–7.63 (m, 1H), 7.62–7.53 (m, 3H), 7.50–7.41 (m, 1H), 4.32–4.20 (m, 1H), 3.99 (s, 3H), 3.95–3.85 (m, 1H), 3.60–3.43 (m, 2H), 3.32–3.20 (m, 1H), 3.15–2.94 (m, 2H), 2.91–2.77 (m, 2H), 2.75–2.65 (m, 3H), 2.63–2.50 (m, 2H), 2.20–1.68 (m, 7H), 1.50–1.40 (m, 3H), 1.35–1.24 (m, 5H); 19F NMR (282 MHz, CDCl3) δ −63.1, −76.3; ESI MS m/z 608 [C31H40F3N3O4S+H]+.1.

Provenance & Evidence