[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=3)[O:17][CH:18]([CH3:21])[C:19]#[N:20])=[N:9]2)=[CH:4][CH:3]=1.C([Sn]([N:38]=[N+:39]=[N-:40])(CCCC)CCCC)CCC.C(OCC)C.C(O)C>C(Cl)Cl.C(O)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=3)[O:17][CH:18]([C:19]3[NH:40][N:39]=[N:38][N:20]=3)[CH3:21])=[N:9]2)=[CH:4][CH:3]=1A mixture of the propanonitrile (110 g) from Step 2 and tri-butyltin azide (120 g) was heated at 130° for 3 hours. The residue was dissolved in CH2Cl2 (1 L) on a steam bath. This solution was added to a mixture of diethylether (2 L), ethanol (100 ml) and acetic acid (10 ml). This mixture was evaporated under vacuo to approximately 300 ml. The residue was triturated with ether (1.5 L), ethyl acetate (600 ml) and filtered. The yellow solid was dissolved in 2 N NaOH (150 ml) and H2O (1 L). The aqueous solution was extracted with ethyl acetate (100 ml). The aqueous solution was then acidified with AcOH (100 ml) in ethyl acetate (100 ml). The mixture was stirred 30 min and filtered to give title compound. m.p. 100°-103°.
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