Hydrochloric Acid → HCID 11236684, compound

Participants

Reaction Steps

(S)-2-{3-[4-(4-Chloro-phenoxy)-phenyl]-ureido}-3-phenyl-propionic acid tert-butyl ester. To a stirred solution of (S)-2-amino-3-phenyl-propionic acid tert-butyl ester (0.2 g, 0.9 mmol) in DMSO (2 mL) was added [4-(4-chloro-phenoxy)-phenyl]-carbamic acid phenyl ester (0.3 g, 0.9 mmol). The mixture was stirred at rt overnight. EtOAc (80 mL) was then added, along with 0.1 N HCl (5 mL). The organic layer was washed sequentially with H2O (10 mL), 1 N NaOH (10 mL) and brine (20 mL), and dried (MgSO4). The solvent was removed. Purification by column chromatography [0–20% of (1% NH4OH/MeOH)/CH2Cl2] afforded 0.35 g (83%) of the desired product. MS (electrospray): mass calculated for C26H27ClN2O4, 466.17; m/z found, 411.1 [M−tBu+H]+. 1H NMR (400 MHz, CDCl3): 7.22–7.13 (m, 5H), 7.10–7.07 (m, 4H), 6.82–6.78 (m, 4H), 6.70 (s, 1H), 4.66 (s, 1H), 3.03 (dd, J=13.9, 6.06 Hz, 1H), 2.94 (dd, J=13.8, 6.07 Hz, 1H), 1.37 (s, 9H).

Provenance & Evidence