3-[5-(3,5-bis-Trifluoromethyl-benzoyl)-2-nitro-phenyl]-2-tert-butoxycarbonylamino-propionic Acid Tert-Butyl Ester → 3-[2-Amino-5-(3,5-bis-Trifluoromethyl-benzoyl)-phenyl]-2-tert-butoxycarbonylamino-propionic Acid Tert-Butyl Ester

Participants

Reaction Steps

The nitrobenzophenone derivative 52 (0.7475 g, 1.23 mmol), isopropanol (40 mL), and 10% palladium on activated carbon (131 mg, 0.131 mmol) were added to a single-necked 200 mL pear-shaped round-bottom flask. The flask was sealed with a rubber septum and charge-purged three times using a hydrogen-filled balloon followed by house vacuum. The reaction vessel was equipped with two hydrogen-filled balloons and allowed to stir at room temperature for exactly 15 minutes. During this time a filter funnel was prepared with celite and packed with isopropanol. The reaction mixture was immediately vacuum filtered through the funnel into a 100 mL round-bottom flask. The solvent was removed in vacuo and the crude mixture was purified by flash chromatography (20% EtOAc:hexanes) to afford 58 as a yellow solid (0.631 g, 89%): m.p. 134–135° C.

Provenance & Evidence