Toluene → (R)-3-((R)-2-amino-3-(1-(hydroxymethyl)cyclopropylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate

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Reaction Steps

To a solution of (R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(1-(hydroxymethyl)-cyclopropylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate (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 (R)-3-((R)-2-amino-3-(1-(hydroxymethyl)cyclopropylamino)-3-oxopropylthio)propane-1,2-diyl didodecanoate as an off white solid. 1H NMR (CDCl3): δ 7.85 (br s, 1H), 5.11-5.18 (m, 1H), 4.36 (dd, 1H), 4.14 (dd, 1H), 4.05 (br s, 1H), 3.59 (q, 2H), 3.50 (dd, 1H), 3.06 (dd, 1H), 2.80 (dd, 1H), 2.68-2.76 (m, 2H), 2.32 (q, 4H), 1.51-1.68 (m, 4H), 1.19-1.35 (m, 32H), 0.90-0.94 (m, 2H), 0.88 (t, 6H), 0.79-0.83 (m, 2H). LRMS [M+H]=629.5.

Provenance & Evidence