Hydrochloric Acid → 7750-45-0

Participants

Reaction Steps

Nα -BOC-Nε -CBZ-L-lysine tert-butyl ester (2) (34.51 g, 79.15 mmol) was dissolved in a mixture of 300 ml absolute EtOH and 1 N HCl (88 ml). Prior to the introduction of H2 gas, 10% Pd--C (2.95 g) was added. After 7 hours, additional catalyst (1.0 g) was added. After 5 hours, the black suspension was filtered through a bed of Celite and washed with EtOH. The filtrate was concentrated and the residue dried under high vacuum to give the Nα -BOC-L-lysine tert-butyl ester as its hydrochloride salt (3) (26.59 g, 99%). 1H NMR (CD3OD) δ3.95 (dd, 1H, J=8.8, 5.0 Hz), 2.93 (t, 2H, J=7.7 Hz), 1.84-1.60 (m, 6H), 1.45 (s, 9H), 1.43 (s, 9H); 13C NMR (CD3OD) δ173.5, 158.2, 82.7, 80.5, 79.5, 55.5, 40.6, 32.1, 28.7, 28.3, 23.9. HRMS m/z calcd. for C15H31N2O4 303.2284, found 303.2272. [α]26D -10.1° (c=1.00, CH3OH).

Provenance & Evidence