Hydrochloric Acid → HCID 11259662, compound

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Reaction Steps

(E)-(S)-4-[3-(4-Phenoxy-phenyl)-ureido]-5-phenyl-pent-2-enoic acid. To a solution of (E)-(S)-4-tert-butoxycarbonylamino-5-phenyl-pent-2-enoic acid (Example 11, step A) (2.12 g, 7.26 mmol) in CH2Cl2 (73 mL) was added 4 M HCl in 1,4-dioxane (25 mL), and the resulting solution was stirred at rt for 15 min. The solvent was removed. To a solution of the resulting residue and TEA (0.74 g, 7.26 mmol) in THF (73 mL) cooled to 0° C., was added 4-phenoxy phenyl isocyanate (1.53 g, 7.26 mmol), and the mixture was stirred for 30 min. The solution was brought to rt and was stirred for an additional 3 h. The solvent was removed, and the resulting yellow oil was purified by column chromatography on silica gel using a gradient of 0–35% (MeOH (10% acetic acid)/CH2Cl2). The purified product was recrystallized from CH2Cl2 and was washed with hexanes to afford 1.45 g (50%) of the desired product as a grey solid. Rf=0.47 (5% MeOH (1% NH4OH)/CH2Cl2). MS (electrospray): mass calculated for C24H22N2O4, 402.16; m/z found, 403.1 [M+H]+, 425.1 [M+Na]+, 827.3 [2M+Na]+. 1H NMR (400 MHz, DMSO-d6): 12.34 (br s, 1H), 8.51 (s, 1H), 7.40–7.20 (m, 9H), 7.08–7.05 (m, 1H), 6.93–6.91 (m, 4H), 6.86 (d, J=5.0 Hz, 1H), 6.35 (d, J=8.5 Hz, 1H), 5.77 (dd, J=15.6, 1.6 Hz, 1H), 4.70–4.61 (m, 1H), 2.93 (dd, J=13.7, 6.1 Hz, 1H), 2.84 (dd, J=13.7, 7.9 Hz, 1H).

Provenance & Evidence