N-[(1,1-Dimethylethoxy)carbonyl]-3-[(2-nitrophenyl)amino]-L-alanine → (2S)-3-[(2-aminophenyl)amino]-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

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Reaction Steps

A solution of (S)-2-tert-butoxycarbonylamino-3-(2-nitro-phenylamino)-propionic acid (Aldrich) (10 g, 30.76 mmol) in MeOH (100 mL) was purged with argon for 30 min, and 10% Pd—C (1 g) was added to the solution. The resulting mixture was hydrogenated using a balloon for 18 h at RT. The mixture was filtered through Celite and the filtrate was concentrated and the resulting material was triturated with hexane to afford (S)-3-(2-amino-phenylamino)-2-tert-butoxycarbonylamino-propionic acid (8.5 g, 93%) as brown solid. LC-MS: 296 (M+H).

Provenance & Evidence