[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:21]N1C(=O)CCC1=O>C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[CH2:9][CH2:10][C:11]2[CH:19]=[C:18]([Cl:21])[CH:17]=[CH:16][C:12]=2[NH:13][C:14]1=[O:15])([CH3:4])([CH3:2])[CH3:3]A round-bottom flask containing ((R)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)-carbamic acid tert-butyl ester (3.09 g, 11.2 mmol) was fitted with a stirbar and septa and flushed with nitrogen. N,N-Dimethylformamide (30 mL) was added, giving a solution that was cooled to 0° C. N-Chlorosuccinimide (2.20 g, 16.5 mmol) was then added, and stirring was continued for 24 hours. The reaction was then poured into ethyl acetate (200 mL) and washed with 1:1 H2O:saturated aqueous NaCl solution (2×100 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give a solid that was purified via flash chromatography on silica gel (5% to 30% ethyl acetate/hexanes linear gradient) to give the desired product.
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