[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([O:30][CH3:31])=[C:8]([C:19]([CH2:22][S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:21]=2)[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:2]1.[N:32]#[C:33][NH2:34].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(#N)C>[C:33]([N:34]=[S:23]([CH2:22][C:19]1[C:8]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])=[C:7]([O:30][CH3:31])[C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[CH:21][CH:20]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)#[N:32]A solution of benzyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoate (Intermediate 226, 0.96 g), cyanamide (0.19 g) and iodobenzene diacetate (0.79 g) in acetonitrile (20 ml) was stirred for 16 hours. The mixture was evaporated to dryness and the residue was purified by chromatography on silica eluting with ethyl acetate and DCM with a gradient of 0-5% to give benzyl 6-[(N-cyano-S-phenylsulphinimidoyl)methyl]-3-(furan-3-yl)-2-methoxybenzoate (0.17 g) as a colourless gum.
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