Diisopropylethylamine → HCID 86597506, compound

Participants

Reaction Steps

Vancomycin hydrochloride (317 mg, 0.213 mmol) and glycine methyl ester hydrochloride (54 mg, 0.426 mmol) are dissolved in 2 mL DMSO and 2 mL DMF and stirred at 0° C. Diisopropylethylamine (186 μL, 0.3195 mmol) is added to the reaction vessel via syringe followed by HOBt/HBTU (710 μL 0.45M DMF solution, 0.319 mmol). The ice bath is removed after addition. After 10 minutes, the reaction is completed and the reaction solution is directly loaded to a poly(divinylbenzene) column (30 mm×8 cm, 50-100 micron particle size) and eluted with methanol/water (0, 10%, 20%, 30%, 40%, 50% of 100 mL each). The fractions containing the pure products are combined and evaporated to give 249 mg of (CXXIX) as a white powder, 77%. Rf=0.15 (CHCl3:MeOH:H2O=3:2:0.5). Mass Spec. [M+H]+, 1521; [M−V]+, 1377.

Provenance & Evidence