(R)-3-((R)-2-amino-3-(6-(benzyloxy)-6-oxohexylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate → 6-((R)-2-amino-3-((R)-2,3-bis(dodecanoyloxy)propylthio)propanamido)hexanoic acid

Participants

Reaction Steps

To a solution of (R)-3-((R)-2-amino-3-(6-(benzyloxy)-6-oxohexylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate in EtOH (0.1 M) was added palladium black (2 eq). The reaction mixture was stirred under hydrogen (1 atm) overnight. The palladium was filtered off and the filtrate was concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH/DCM to give the product as an off-white solid. 1H NMR (CDCl3): δ 7.33 (t, 1H), 5.06-5.15 (m, 1H), 4.30 (dd, 1H), 4.08 (dd, 1H), 3.43 (dd, 1H), 3.20-3.31 (m, 1H), 3.09-3.19 (m, 1H), 3.04 (dd, 1H), 2.61-2.74 (m, 3H), 2.21-2.31 (m, 6H), 1.84-2.06 (m, 3H), 1.40-1.63 (m, 8H), 1.28-1.37 (m, 2H), 1.12-1.28 (m, 32H), 0.81 (t, 6H). LRMS [M+H]=673.5.

Provenance & Evidence