Cl[C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12](=O)([O-])[O-].[K+].[K+].C(O)C.[NH2:21][CH:22]([C:25]([OH:27])=[O:26])[CH2:23][OH:24]>O>[CH3:12][O:26][C:25](=[O:27])[CH:22]([CH2:23][OH:24])[NH:21][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]To 15.66 g of 1-fluoro-2-nitrobenzene (VII), 16.87 g of potassium carbonate, 100 ml of 95% ethanol, and 40 ml of water are added 11.66 g of DL-serine. The reaction is stirred at 90° overnight and then cooled. The solvents are removed under vacuum and the residue is azeotroped with toluene to remove residual water. The resulting solid is washed with ether and toluene to remove unreacted 1-fluoro-2-nitrobenzene. The solid is then stirred for 18 hr at 20°-25° in 80 ml of DMF with 15.34 g of potassium carbonate and 24 ml of iodomethane. Excess iodomethane and DMF are then removed under vacuum and the residue is partitioned between a mixture of methylene chloride, chloroform and water. The organic layers are dried over sodium sulfate and concentrated. Ethyl ether and hexane are added to the residue and the solid is collected and dried to give the title compound, mp 138°-140°; NMR (CDCl3) 2.15, 3.83, 4.10, 4.41, 6.73-6.81, 7.46, 8.22, 8.60 δ.
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