[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=CC=1S(N)(=O)=O)([OH:3])=[O:2].O[N:15]1C(=O)CC[C:16]1=O.[CH3:22]CN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.C[N:44]([CH:46]=[O:47])C>>[CH3:22][CH:8]([CH2:9][C@H:4]([NH:44][C:46]([CH2:16][NH2:15])=[O:47])[C:1]([OH:3])=[O:2])[CH3:7]Carboxy benzene sulfonamide (20 μmol in 20 μL dry DMF (J. T. Baker), N-hydroxysuccinimide (22 μmol in 22 μL dry DMF), and EDC-HCl (14 μmol in 140 μL dry DMF) were mixed together and stirred at room temperature for 4 hours. The dipeptide H-leucine-glycine-OH (2 μmol in 20 μL dry DMF) and DIPEA (1.2 μL, 8 μmols) were added and the resulting mixture was stirred overnight at room temperature. ESI-MS calculated for [M−H+]−: 370.41 Found: 369.97. 1H NMR (DMSO-d6, 500 MHz) δ 8.72 (d, 1H, J=8.5 Hz), 8.30 (t, 1H, J=5.5 Hz), 8.09 (d, 2H, J=8 Hz), 7.94 (d, 2H, J=8 Hz), 7.52 (s, 2H), 4.61 (m, 1H), 3.77 (m, 2H), 1.72 (m, 2H), 1.62 (m, 1H), 0.95 (d, 3H, J=6.5 Hz), 0.92 (d, 3H, J=6.5 Hz). 13C NMR (DMSO-d6, 125 MHz) δ 173.0, 171.8, 166.0, 147.0, 137.7, 128.9, 126.2, 52.4, 41.5, 41.0, 25.1, 23.8, 22.0.
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