Triethylamine → HCID 66666644, compound

Participants

Reaction Steps

A mixture of (R)-1-(4-(3-(2-methylpyridin-4-yl)-3-oxo-1-o-tolylpropyl)phenyl)-piperidine-4-carboxylic acid (example 367, step 1; 100 mg, 226 μmol) triethylamine (68.6 mg, 94.5 μl, 678 μmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (79.8 mg, 249 μmol) in tetrahydrofuran (5 mL) was stirred at room temperature for 15 min, then treated with methyl 2-aminoacetate hydrochloride (42.6 mg, 339 μmol). The reaction mixture was stirred for 20 h at room temperature, then partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated to afford the crude title compound (130 mg), which was directly used in the next step. Yellow oil, MS (ESI+): m/z=514.6 ([M+H]+).

Provenance & Evidence