F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([O:13][C:14](=[O:21])[CH2:15][C@@H:16]([NH2:20])[CH2:17][CH2:18][CH3:19])[CH3:12].C(N(C(C)C)CC)(C)C.O>CN(C=O)C>[CH2:11]([O:13][C:14](=[O:21])[CH2:15][C@@H:16]([NH:20][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH2:17][CH2:18][CH3:19])[CH3:12]
To a solution of 1-fluoro-2-nitrobenzene (500 mg, 3.5 mmol) in DMF (150 mL) were added (S)-3-Amino-hexanoic acid ethyl ester (600 mg, 3.8 mmol) and diisopropyl ethylamine (0.65 mL, 3.8 mmol). The solution was heated to 90 C for 16 hours. The solution was cooled down and was water (300 mL) was added. The solution was extracted with EtOAc and the combined organic layer was dried with MgSO4. The mixture was filtered and the filtrate was concentrated. The residue was purified by CombiFlash with 5% EtOAc in Hexane as the eluent to afford the desirable product (S)-3-(2-Nitro-phenylamino)-hexanoic acid ethyl ester (795 mg, 80%) as a colorless oil.
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