C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[O:18]=[C:19]1[NH:23][C@H:22]([C:24]([OH:26])=O)[CH2:21][O:20]1.[N+]([O-])(O)=O.[N+:31]([O:34][CH2:35][CH2:36][NH2:37])([O-:33])=[O:32]>O1CCCC1>[N+:31]([O:34][CH2:35][CH2:36][NH:37][C:24]([C@@H:22]1[CH2:21][O:20][C:19](=[O:18])[NH:23]1)=[O:26])([O-:33])=[O:32]3.2 ml of triethylamine and 1.5 ml of diethyl cyanophosphonate were added, whilst ice-cooling, to a suspension of 1.0 g of (4S)-2-oxooxazolidine-4carboxylic acid and 1.55 g of N-(2-nitrooxyethyl)amine nitrate in 20 ml of dry tetrahydrofuran, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was diluted with ethyl acetate; the mixture was then washed with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residual brown oil thus obtained was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give the title compound as yellowish brown crystals. These crude crystals were recrystallized from ethyl acetate, to give 0.25 g of the title compound as colorless needles, melting at 102°-103° C.
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