Trifluoroacetic acid → n1-[1-(4-Biphenylyl)-2-(1-pyrrolidinyl)ethyl]-n2-(3,4-dichlorophenyl)-n1-methyl-n2-[2-(methyloxy)ethyl]glycinamide

Participants

Reaction Steps

N-(3,4-dichlorophenyl)-N-[2-(methyloxy)ethyl]glycine, lithium salt (100 mg, 0.35 mmol) [1-(4-biphenylyl)-2-(1-pyrrolidinyl)ethyl]methylamine (98 mg, 0.35 mmol), triethylamine (73 uL, 0.53 mmol), and (1H-1,2,3-benzotriazol-1-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (BOP Reagent, 186 mg, 0.42 mmol) were added in that order to a 4 mL screw capped vial that contained 1 mL of anhydrous DMF. The reaction mixture was stirred for 20 hours at room temperature, after which time HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid) showed that the reaction was complete. The solvent was removed under vacuum and the residue was dissolved in 2 mL of DMSO, filtered through a 0.2 um PTFE Acrodisk, and purified by reverse-phase HPLC (Xterra Prep RP, 30×150 mm, 35 mL/min, A: acetonitrile B: water (adjusted to pH 10 with NH40H), A: 35 to 99% over 14 min, UV detection at 214 nm) to give the title compound (117 mg, 0.216 mmol, 61%) as a white solid. MS (ES) m/e 540 [M+H]+.

Provenance & Evidence