A flask was charged with 2-amino-3-benzyloxy-N-(4-phenoxyphenyl)propanamide (150 mg, 0.42 mmoles), prepared as in Reference 5, 1H-imidazol-4-ylacetic acid hydrochloride (81 mg, 0.50 mmoles), HATU (188 mg, 0.50 moles) and DMF (1 mL). DIEA (370 μL, 2.1 mmoles) was added and the mixture was stirred at ambient temperature for 18 hours. The reaction mixture was partitioned between ethyl acetate and deionized H2O. The aqueous layer was separated and extracted with ethyl acetate. The combined organic layer was washed with 5% lithium chloride (3×5 mL), 1N sodium bicarbonate (2×5 mL) and then deionized water (2×5 mL) and concentrated in vacuo. Product was purified from the residue by preparative HPLC (ammonium acetate/acetonitrile). The purified product was taken up into methanol and the solution was neutralized with basic resin, filtered and concentrated in vacuo to give Compound 142, 2-(2-(1H-imidazol-5-yl)acetamido)-3-benzyloxy-N-(4-phenoxyphenyl)propanamide (118 mg, 60% yield), as a white solid. 1H-NMR (400 MHz, CDCl3): 9.23 (s, 1H), 7.53-7.40 (m, 4H), 7.35-7.27 (m, 6H), 7.08 (t, 1H), 7.00-6.92 (m, 3H), 6.87 (s, 1H), 4.77 (m, 1H), 4.55 (dd, 2H), 4.18 (dd, 1H), 3.70-3.58 (m, 3H). MS (EI) for C27H26N4O4. found 471.0 (MH+).
