(2S,3S)-2-tert-butoxycarbonylamino-3-(5-methyl-2-nitro-phenoxy)-butyric acid → (2S,3S)-3-(2-amino-5-methyl-phenoxy)-2-tert-butoxycarbonylamino-butyric acid

Participants

Reaction Steps

(2S,3S)-2-tert-butoxycarbonylamino-3-(5-methyl-2-nitro-phenoxy)-butyri c acid (0.95 g, 2.68 mmol, Eq: 1.00) and 5% Pd/C (200 mg, 94.0 μmol, Eq: 0.0351) in EtOH (100 mL) were hydrogenated overnight at RT and ambient pressure and an additional portion of 10% Pd/C (100 mg, 47.0 μmol, Eq: 0.0176) was added. After 2 h the mixture was filtered through Celite, the filtrate was concentrated and the residue was purified by silica gel chromatography to afford (2S,3S)-3-(2-amino-5-methyl-phenoxy)-2-tert-butoxycarbonylamino-butyric acid (294 mg, 34%) as a solid.

Provenance & Evidence