Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH2:13])[CH2:11][NH2:12])=[CH:6][CH:5]=1.[OH-:14].[Na+].[O:16]1[CH2:22][C:21](=O)[CH2:20][O:19][CH2:18][CH2:17]1.[CH:24](Cl)(Cl)Cl.Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[NH:13][C:24](=[O:14])[C:21]3([CH2:22][O:16][CH2:17][CH2:18][O:19][CH2:20]3)[NH:12][CH2:11]2)=[CH:8][CH:9]=1
0.68 g (3.0 mmol) 1-(4-fluorophenyl)ethane-1,2-diamine dihydrochloride were placed with 32 mg (0.14 mmol) benzyltriethylammonium chloride in 6 ml dichloromethane and cooled with ice/acetone. Then 1.0 ml (19 mmol) 50% sodium hydroxide solution were added. At 0° C. 0.44 g (3.0 mmol) 80% [1,4]dioxepan-6-one were added dropwise together with 0.37 ml (4.6 mmol) chloroform and 5 ml dichloromethane. The reaction mixture was left overnight to warm up to RT. Then the reaction mixture was acidified with an aqueous 4N hydrochloric acid solution. The phases were separated. The aqueous phase was made alkaline with a 4N sodium hydroxide solution and extracted with ethyl acetate. The combined organic phases were dried and evaporated to dryness by rotary evaporation. Purification was carried out by flash chromatography.
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