Sodium Iodide → Ethyl[3-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-yl]acetate

Participants

Reaction Steps

A mixture of TMSCl (0.513 mL), sodium iodide (601 mg) and acetonitrile (9 ml) was added to a stirred suspension of Intermediate 15 (420 mg) in acetonitrile (3 ml). The RM was stirred at room temp under nitrogen overnight. The reaction mixture was partitioned between EtOAc (50 ml) and sat. NaHCO3 aq. sol.: water (1:1, 50 ml). The two phases were separated and the aqueous phase was extracted again with EtOAc (50 ml). The phases were separated; the organic extracts were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified by reverse phase chromatography using an acetonitrile—0.1% NH3:water—with an amonium carbonate buffer modifier (pH=10) 5%-35% gradient. The desired fractions were combined and concentrated under vacuum. The mixture was purified by MDAP (Method B). The desired fractions were combined and concentrated under nitrogen blowdown to give the title compound (22 mg). LC/MS MH+ 403 Rt 1.09 min (2 minute run).

Provenance & Evidence