HCID 86664896, compound → HCID 178472509, compound

Participants

Reaction Steps

Ethyl (1S,2S)-2-[4-(1-trityl-1H-imidazol-4-yl)phenyl]cyclopropanecarboxylate (4.1 g, from Step 1) was suspended in 30 mL of methanol and 30 mL of 1N HCl. The reaction mixture was heated at reflux for 2 hours. The solvent was evaporated in vacuo and the residue was triturated with ether (100 mL). The liquid organic layer was discarded. The solid was the desired product HCl salt. To the solid were added 100 mL EtOAc and 13 mL of 1N NaOH to release the free base. The aqueous/organic mixture was shaken in a separation funnel. The aqueous layer was discarded, and the organic layer was washed with brine, dried with MgSO4, filtered, and concentrated in vacuo to give the title compound (1.4 g, 66.4%). 1H NMR (500 MHz, (CD3OD): 7.98 (s, 1H), 7.58 (d, 2H), 7.39 (s, 1H), 7.17 (d, 2H), 4.18 (q, 2H), 2.43 (m, 1H), 1.86 (m, 1H), 1.57 (m, 1H), 1.37 (m, 1H), 1.24 (t, 3H). LCMS: ink 257 (M+H)+.

Provenance & Evidence