C(N(CC)CC)C.[C:8]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)(=[O:13])[CH2:9][C:10]([CH3:12])=[O:11].C1(C)C=CC(S([N:34]=[N+:35]=[N-])(=O)=O)=CC=1>C(#N)C>[N+:34](=[C:9]([C:10](=[O:11])[CH3:12])[C:8]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=1)=[O:13])=[N-:35]35.0 ml (0.25 mole - 1.8 equivalent) of triethylamine were added dropwise to a solution, which had been cooled to 0° C., of 33.18 g (0.14 mole) of 4-nitrobenzyl acetoacetate and 30.40 g (0.15 mole) of p-toluenesulphonyl azide in 280 ml of anhydrous acetonitrile. The mixture was stirred at 0° C. for 2 h, and then the resulting precipitate was filtered off with suction, washed with ether and dried over P4O10 under high vacuum. 20.3 g (55%) of the title compound were obtained as colorless crystals, melting point 132° C. A further 6.3 g (17%) of the title compound were obtained by chromatography of the filtrate solution on 400 g of silica gel (toluene:ethyl acetate 9:1), Rf: 0.35 (toluene:ethyl acetate 9:1).
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