(S)-2-((tert-butoxycarbonyl)amino)-3-(2-nitrophenoxy)propanoic acid → (S)-3-(2-aminophenoxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Beteiligte Stoffe

Reaktionsschritte

A mixture of (S)-2-tert-butoxycarbonylamino-3-(2-nitro-phenoxy)-propionic acid (7.6 g, 23.3 mmol, leq) and 10% Pd/C (496 mg) in MeOH (215 mL) was hydrogenated at 1 atm for 2 h. After the theoretical uptake of hydrogen, the reaction mixture was filtered through Celite and washed with MeOH. The filtrate was concentrated and the residue was tritrurated with hexanes to give a solid that was filtered and washed with hexanes to give (S)-3-(2-amino-phenoxy)-2-tert-butoxycarbonylamino-propionic acid (3.8 g, 55%) as a white solid which was used without purification.

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