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N-Glycinamide oxazolidinones are key intermediates for the synthesis of a new class of peptidomimetics. We report, herein, the synthesis of a series of 3,4,5-trisubstituted oxazolidinones with a glycine residue at N-3 of the oxazolidinone ring. Substituents at C-4 and C-5 contain substitution capabilities which are amenable for the introduction of additional peptide chains. The synthesis of the key N-Glycinamide oxazolidinone is made possible through two reactions; a tandem aziridine ring opening/oxazolidinone alkylation and, subsequently, a fused-lactone ring opening by an amine which leads to the N-Glycinamide oxazolidinones.

Routes to N-glycinamide oxazolidinone derivatives: The reaction of 4-trityloxymethyl-3-oxa-1-azabicyclo[3.1.0]hexan-2-one with active halides