(S)-3-(2-benzyloxy-4-nitro-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester → (S)-3-(4-amino-2-hydroxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester

Participants

Reaction Steps

(S)-3-(2-Benzyloxy-4-nitro-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester (150 mg, 0.28 mmol) was hydrogenated with 10% Pd/C (50 mg) in 1:1 tetrahydrofuran/ethanol (10 mL) at room temperature under 50 psi hydrogen in a Parr shaker for 3 h. The reaction mixture was filtered over a celite pad, the catalyst was washed with ethanol, the organics were combined and the solvent was removed under reduced pressure to give (S)-3-(4-amino-2-hydroxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester, 100 mg, 85%. RP-HPLC (10 to 90% acetonitrile in 0.1 N aqueous ammonium acetate over 10 min at 2 mL/min using a Waters Symmetry C18 150×4.6 mm column) 8.3 min.

Provenance & Evidence