Trifluoroacetic acid → HCID 17984356, compound

Participants

Reaction Steps

A solution of 3-{2-aminomethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid tert-butyl ester acetic acid salt (290 mg, 0.665 mmol, Example 1, Step B) and 2-benzoyl-cyclohexanone (161 mg, 0.797 mmol) in anisole (20 mL) was treated with a slurry of Pd/C (60 mg) in anisole (2 mL). The mixture was refluxed at 200° C. with azeotropic removal of water for 2 h and cooled to room temperature. The catalyst was filtered and a fresh slurry of Pd/C (60 mg) in anisole was added. The mixture was heated at 110° C. for 72 h and filtered through a pad of Celite. The filtrate was concentrated, purified by silica gel chromatography-(25% EtOAc/hexanes) to afford a mixture of starting material and desired tert butyl ester intermediate. The mixture was treated with TFA (1.0 ml)/CH2Cl2 (1.0 ml)/H2O (0.1 mL), stirred for 3 h, and concentrated. The residue was and purified using silica gel chromatography (MeOH/EtOAc 1/9) to give the title compound (38 mg, 10%). MS (ESI) m/z 561.3 (M+H)+.

Provenance & Evidence