[N:1]1([CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH3:44][O:45][C:46](=[O:51])[C@H:47]([CH2:49][OH:50])[NH2:48]>CN(C=O)C>[N:1]1([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:48][C@H:47]([C:46]([O:45][CH3:44])=[O:51])[CH2:49][OH:50])=[O:17])=[CH:18][CH:19]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1A stirred solution of 4-[(1H-benzoimidazol-1-yl)methyl]benzoic acid (4 g, 15.87 mmol) in DMF at 0° C. is treated sequentially with EDC (3.6 g, 19 mmol), HOBt (2.5 g, 19 mmol), DIPEA (5.1 g, 39.5 mmol, 2.5 eq) and serine methyl ester hydrochloride (2.9 g, 19 mol), stirred at room temperature overnight and evaporated to dryness. The resultant residue is dissolved in EtOAc and water. The layers are separated and the organic layer is washed successively with 1M HCl, water, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to give the title product in 64% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, DMSO-d6): 8.23-8.26 (m, 2H); 7.9 (s, 2H); 7.87 (d, J=7.6 Hz, 2H); 7.70 (d, J=6 Hz, 1H); 7.33 (m, 3H); 7.20 (m, 2H); 5.54 (s, 2H); 4.90 (t, J=4 Hz, 1H); 4.60 (m, 1H); 3.84-3.90 (m, 2H); 3.70 (s, 3H). LCMS (ESI+) 354 (MH+).
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