Benzyl (R)-3-((R)-2,3-didodecanamidopropylthio)-1-(1-(hydroxymethyl)cyclopropylamino)-1-oxopropan-2-ylcarbamate → N,N'-((R)-3-((R)-2-amino-3-(1-(hydroxymethyl)cyclopropylamino)-3-oxopropylthio)propane-1,2-diyl)didodecanamide

Participants

Reaction Steps

Benzyl(R)-3-((R)-2,3-didodecanamidopropylthio)-1-(1-(hydroxymethyl)cyclopropylamino)-1-oxopropan-2-ylcarbamate (1 eq) was stirred in dry EtOH (0.05 M) under N2 at room temperature. Pd(OH)2 (2.1 eq) was then added in one portion. The reaction was then stirred under hydrogen atmosphere (1 atm) until complete reduction was observed. The crude reaction was filtered twice through celite and cotton, then the organics concentrated and purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 0-10% MeOH/DCM to afford N,N′—((R)-3-((R)-2-amino-3-(1-(hydroxymethyl)cyclopropylamino)-3-oxopropylthio)propane-1,2-diyl)didodecanamide as an oil. 1H NMR (CDCl3): δ 8.02 (s, 1H), 6.83 (t, 1H), 6.70 (t, 1H), 3.50-3.71 (m, 6H), 3.00-3.12 (m, 3H), 2.88-2.94 (m, 2H), 2.21 (t, 4H), 1.64 (t, 4H), 1.21-1.35 (m, 32H), 0.93 (m, 4H), 0.82 (t, 6H). LRMS [M+H]=628.0.

Provenance & Evidence