Many diseases that plague developing countries often go neglected due to pharmaceutical companies irrecoverable costs. However, researchers at Indiana University Purdue University Indianapolis (IUPUI) are working to fix this issue by linking academic training to drug discovery through the Distributed Drug Discovery (D3) program. One part of D3 includes the synthesis of acylated unnatural amino acid amides through techniques known to undergraduates. Previous studies have shown that trifluoroacetic acid (TFA)-mediated cleavage of Rink resin-bound N-acylated amino acid amides produce a mixture of the primary amide and the undesired carboxylic acid from partial hydrolysis of the amide products. The hydrolysis to the acid can be suppressed by use of cleavage cocktails containing 65% or less of TFA or by performing the cleavage at -20�C with 95/5 TFA/water. Utilizing Quantitative Nuclear Magnetic Resonance (QNMR), we examined these various methods of TFA-mediated cleavage and determined the overall yield of the products.

Solid phase synthesis of <i>N</i>-acylated amino acid amides using Rink resin

245th National Meeting (2013)

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Solid phase synthesis of N-acylated amino acid amides using Rink resin