[Br:1][CH2:2][C:3](Br)=[O:4].[C:6]([O:10][C:11](=[O:24])[NH:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>C(Cl)Cl>[C:6]([O:10][C:11](=[O:24])[NH:12][CH2:13][CH2:14][N:15]([C:3](=[O:4])[CH2:2][Br:1])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:9])([CH3:7])[CH3:8]To a solution of bromoacetyl bromide (0.25 mL, 2.92 mmol) in CH2Cl2 (10 mL) at -10° C. was added a solution of 2-(phenylethylamino)ethyl carbamic acid tert-butyl ester (0.7 g, 2.65 mmol) and triethylamine (0.41 mL, 2.92 mmol) in CH2Cl2 (10 mL) dropwise. The mixture was stirred at -10° C. for 30 min, before removal of the solvent in vacuo. The residue was partitioned between EtOAc (2×30 mL) and water (30 mL). The combined organic layers were dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with petrol:EtOAc (2:1→1:1), to afford the title amide (0.81 g, 79%) as a colourless oil. 1H NMR (250 MHz, CDCl3) δ 1.44 (9H, s), 2.86-2.94 (2H, m), 3.10-3.94 (8H, m), 4.59 and 4.92 (1H, 2×br s), 7.15-7.37 (5H, m). MS (ES+) (385/387, M+).
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