(C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OCH2Ph → (C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OH

Participants

Reaction Steps

(C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OCH2Ph (1.0 g, 1.1 mmol) was dissolved in absolute ethanol (100 mL), 10% Pd/C (0.2 g) was added, and this mixture was shaken under 70 psi hydrogen pressure for 3 h in a Parr apparatus. The reaction mixture was heated to reflux and filtered through a celite layer and the solvent was evaporated under reduced pressure to leave (C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OH as a white solid (0.86 g, 96%), mp 163–164° C. 1H-NMR (300 MHz, δ, CD3OD): 0.90 (6H, t, J=6.9 Hz), 1.29 (64H, m), 1.57 (4H, bs), 3.21 (2H, t, J=7.8 Hz), 3.35 (2H, t, J=7.8 Hz), 3.93 (2H, s), 3.94 (2H, s), 3.97 (2H, s), 4.12 (2H, s), 4.40 (2H, s). IR (KBr, cm−1): 1740 (CO), 1650 (CO).

Provenance & Evidence