F[C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Cl.[CH2:13]([O:15][C:16](=[O:23])[CH2:17][CH:18]([NH2:22])[CH2:19][CH2:20][CH3:21])[CH3:14].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:13]([O:15][C:16](=[O:23])[CH2:17][CH:18]([NH:22][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[CH2:19][CH2:20][CH3:21])[CH3:14]To a solution of 3-Fluoro-4-nitrotoluene (1.0 g, 6.5 mmol) in DMF (5 mL) were: 3-Amino-hexanoic acid ethyl ester hydrochloride (1.3 g, 6.7 mmol) and DIPEA (2.2 mL, 12.9 mmol). The reaction mixture was stirred at room temperature for 48 h. The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was then dried over Na2SO4 and concentrated. The resulting residue was purified by Combiflash using hexane and ethyl acetate (10% gradient) as an eluent to afford 1.4 g of the desired product as orange oil.
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