Toluene → N-((R)-1-((R)-2-amino-3-(1-(hydroxymethyl)cyclopropylamino)-3-oxopropylthio)-3-(hexadecyloxy)propan-2-yl)dodecanamide

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Reaction Steps

To a solution of (9H-fluoren-9-yl)methyl(R)-3-((R)-2-dodecanamido-3-(hexadecyloxy)propylthio)-1-(1-(hydroxymethyl)cyclopropylamino)-1-oxopropan-2-ylcarbamate (1 eq) was added 20% piperidine (50 eq) in acetonitrile. The resulting gel was diluted with DCM and sonicated for 3 minutes. The mixture was added to toluene and then concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 100% EtOAc then 0-10% MeOH/DCM to give N—((R)-1-((R)-2-amino-3-(1-(hydroxymethyl)cyclopropylamino)-3-oxopropylthio)-3-(hexadecyloxy)propan-2-yl)dodecanamide. 1H NMR (DMSO d-6): δ 8.13 (s, 2H), 7.73 (d, 2H), 4.68 (t, 2H), 3.89-3.97 (m, 2H), 3.35-3.44 (m, 5H), 3.20-3.24 (m, 1H), 2.59-2.74 (m, 4H), 2.32-2.34 (m, 1H), 2.05 (t, 2H), 1.42-1.50 (m, 4H), 1.21-1.28 (m, 40H), 0.85 (t, 6H), 0.67 (dd, 2H), 0.56 (dd, 2H). LRMS [M+H]=670.6.

Provenance & Evidence