Hydrochloric Acid → HCID 11752425, compound

Participants

Reaction Steps

To a solution of [(S)-1-(2-diisopropylamino-ethylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (Example 3, step B) (0.1 g, 0.258 mmol) in CH2Cl2 (3 mL), a 4 M solution of HCl in dioxane (0.64 mL, 2.56 mmol) was added, and the mixture was stirred for 3 h at rt. The solvents were removed, the residue was treated with CH2Cl2, and the solvent was removed again. The crude product was dissolved in CH2Cl2 (3 mL), and triethylamine (0.037 g, 0.365 mmol) was added at 0° C. followed by 4-phenoxyphenylisocyanate (0.059 g, 0.28 mmol). The mixture was warmed to rt over a period of 2 h and was then diluted with EtOAc (100 mL). The organic layer was washed with saturated NaHCO3 (25 mL) and brine (25 mL), and dried (Na2SO4). The solvent was removed, and the residue was purified by flash column chromatography using 0–20% MeOH (1% NH4OH)/CH2Cl2 to afford 0.07 g (55%) of the desired product. MS (electrospray): mass calculated for C30H38N4O3, 502.29; m/z found, 503.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.3–7.19 (m, 9H), 7.04 (m, 1H), 6.91–6.85 (m, 4H), 4.47 (t, J=7.4 Hz, 1H), 3.19–2.95 (m, 6H), 2.42 (br s, 2H), 1.02 (d, J=6.4 Hz, 12H).

Provenance & Evidence