(2S,3S)-2-(tert-butoxycarbonylamino)-3-(5-cyano-2-nitrophenylamino)butanoic acid → (2S,3S)-3-(2-amino-5-cyanophenylamino)-2-(tert-butoxycarbonylamino)butanoic acid

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A mixture of (2S,3S)-2-(tert-butoxycarbonyl amino)-3-(5-cyano-2-nitrophenylamino)butanoic acid (5.35 g, 14.7 mmol) and PdC (10% dry basis, wet, 50% water) (535 mg, 251 μmol) in MeOH (60 ml) and EtOAc (60 ml) was shaken under H2 (50 PSI) for 4 h, then filtered through a bed of celite and concentrated to afford (2S,3S)-3-(2-amino-5-cyanophenylamino)-2-(tert-butoxycarbonylamino)butanoic acid (4.9 g, quant.) as a dark brown solid.

Provenance & Evidence