tert-Butyl N-((2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylethanoyl)-O-(tert-butyl)-L-serinate → tert-Butyl N-[(2R)-2-amino-2-phenylethanoyl]-O-(tert-butyl)-L-serinate

Participants

Reaction Steps

tert-Butyl N-((2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylethanoyl)-O-(tert-butyl)-L-serinate (Method 5; 3.3 g, 6.8 mmol) was dissolved in EtOH (95%, 30 ml) and a cat amount of Pd/C (5%)(50% in water) was added and hydrogenation was performed at atmospheric pressure for 3 hours at room temperature. The reaction mixture was filtered through diatomaceous earth and the solvent was evaporated to give the title compound (2.35 g, 98%). NMR (500 MHz, CD3OD): 1.1 (s, 9H), 1.45 (s, 9H), 3.45-3.8 (m, 2H), 4.5 (t, 1H), 4.55 (s, 1H), 4.85 (s, 2H), 7.3-7.5 (m, 5H).

Provenance & Evidence