Benzyl Alcohol → HCID 118114472, compound

Participants

Reaction Steps

To a solution of (S)-3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)benzoic acid (100 mg, 0.31 mmol), Et3N (0.17 mL, 1.24 mmol) and benzyl alcohol (0.26 mL, 2.48 mmol) in dioxane (1.5 mL) was added diphenyl phosphoryl azide (93 mg, 0.34 mmol) at room temperature. The resulting mixture was heated to reflux for 24 h, cooled to room temperature and partitioned between EtOAc (30 mL) and water (20 mL). The layers were separated and the organic phase dried over MgSO4. The mixture was filtered and solvent was removed in vacuo. The residue was purified via silica gel chromatography, eluting with 0-20% EtOAc in isohexane, to give the corresponding compound tert-butyl N—[(S)-[3-(benzyloxycarbonylamino)phenyl]-phenyl-methyl]carbamate as a white solid (125 mg). To a solution of the solid (125 mg, 0.29 mg) in EtOAc (4 mL) was added 10% Pd/C (140 mg) and ammonium formate (200 mg, 3.07 mmol). The resulting slurry was refluxed for 2 h. The reaction mixture was then filtered over celite at room temperature, the cake washed with EtOAc (50 mL) and the filtrate concentrated in vacuo. The resulting oil solidified on standing to give the title compound (42 mg, 45% over two steps) as a white solid.

Provenance & Evidence