C(OC(=O)C)(=O)C.[CH:8]([O-:13])([O-])[O:9][CH2:10][CH3:11].[CH3:14][O:15][C:16]1[C:17]([F:32])=[C:18]([CH:27]=[C:28]([F:31])[C:29]=1[F:30])[C:19]([CH2:21][C:22](OCC)=O)=[O:20].[CH:33]1([NH2:36])[CH2:35][CH2:34]1>C(Cl)Cl>[CH:33]1([NH:36][CH:22]=[C:21]([C:19](=[O:20])[C:18]2[CH:27]=[C:28]([F:31])[C:29]([F:30])=[C:16]([O:15][CH3:14])[C:17]=2[F:32])[C:8]([O:9][CH2:10][CH3:11])=[O:13])[CH2:35][CH2:34]13.5 ml of acetic anhydride and 1.1 ml of ethyl orthoformate were added to 1.40 g (0.005 mole) of ethyl 3-methoxy-2,4,5-trifluorobenzoylacetate (XXIX) [prepared as described in Step (E9) above], and the mixture was heated under reflux for 1 hour and then concentrated by evaporation under reduced pressure. 0.38 g (0.006 mole) of cyclopropylamine was added dropwise, whilst ice-cooling and stirring, to a solution of the residue in 10 ml of methylene chloride, and the mixture was stirred for a further 30 minutes. The solvent was then removed by evaporation under reduced pressure from the reaction mixture, and the residue was subjected to silica gel column chromatography eluted with a 9:1 by volume mixture of toluene and ethyl acetate, to afford 1.23 g of ethyl 3-cyclopropylamino-2-(3-methoxy-2,4,5-trifluorobenzoyl)acrylate (XXXI) as a pale brown oily substance.
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