Despite the antibiotic activity and the attractiveness of β-lactams, the solid-phase synthesis of this class of compounds has been barely reported. Now the diastereoselective synthesis of the 1-oxacepham 2 from the resin-bound β-lactam derivative 1 has been achieved in five steps. The synthesis of 2 and other 1-oxacephams is attractive because all the reaction steps proceed in high yield, the purity of the product is high, and the reaction sequence is simple.
Taking the enkephalin synthesis on soluble polyethylene glycol support as a test case, this communication demonstrates the usefulness of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry to monitor each step of coupling as well as removal of the N-terminal protecting group of the polymer-bound growing peptide chain. With minute amounts of sample the high mass accuracy permits detection of side reactions as well as incomplete reaction products. #
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