(R)-2-((tert-Butoxycarbonyl)amino)-3-((2-nitrophenyl)amino)propanoic acid → (R)-2-tert-butoxycarbonylamino-3-(2-aminophenylamino)-propi onic acid

Participants

Reaction Steps

To a solution of (R)-(−)-2-tert-butoxycarbonylamino-3-(2-nitrophenylamino)propionic acid (7.6 g) in tetrahydro-furan (100mL), 10% palladium carbon (1 g) was added, followed by stirring at room temperature for 3 hours under a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure, whereby (R)-2-tert-butoxycarbonylamino-3-(2-aminophenylamino)-propi onic acid was obtained. It was dissolved in toluene (100 mL). The solution was refluxed overnight. The reaction mixture was allowed to cool down and then concentrated under reduced pressure. The residue was purified by silica gel colomn chromatography (ethyl acetate:n-hexane=1:1), whereby the title compound (5.16 g) was obtained. Yield: 80%.

Provenance & Evidence