Triethylamine → HCID 11351277, compound

Participants

Reaction Steps

(R)-2-(3-Biphenyl-4-yl-1-methyl-ureido)-3-phenyl-propionic acid. Triethylamine (0.17 g, 1.68 mmol) was added to a suspension of (S)-2-methylamino-3-phenyl-propionic acid (0.2 g, 1.12 mmol) in 1:1 acetone/H2O (80 mL). Once the (S)-2-methylamino-3-phenyl-propionic acid dissolved, 4-biphenylyl isocyanate (0.228 g, 1.17 mmol) was added as a solution in THF (1.5 mL) at 0° C. As the mixture was warmed to rt, solids crashed out of solution. The mixture was stirred for 7 h at rt, and then the solvents were removed. After acidifying with 1 N HCl (10 mL) to bring the pH to 2, the reaction mixture was filtered, and the aqueous filtrate was extracted with EtOAc (3×40 mL). The combined organic layers were washed with brine and dried (MgSO4), and the solvent was removed. Column chromatography using [5–20% (1% NH4OH/MeOH)/CH2Cl2] afforded 0.1 g (24%) of the desired product. MS (electrospray): mass calculated for C23H22N2O3, 374.16; m/z found, 375.1 [M+H]+, 397.1 [M+Na]+. 1H NMR (400 MHz, CD3OD): 7.63–7.59 (m, 4H), 7.45–7.41 (m, 2H), 7.36–7.29 (m, 4H), 7.23–7.21 (m, 2H), 7.04–7.01 (m, 2H), 4.48 (t, J=4.1 Hz, 1H), 3.37–3.33 (m, 1H), 3.25 (dd, J=14.4, 3.8 Hz, 1H), 3.10 (s, 3H).

Provenance & Evidence