Toluene → HCID 58979111, compound

Participants

Reaction Steps

A 1 mL microvial under a nitrogen atmosphere was charged with 3-(4-{2-[2-(4-bromophenyl)-5-methyloxazol-4-yl]ethoxy}-2-cyclohexylcarbamoyloxymethylphenyl)-propionic acid tert-butyl ester (0.30 g, 0.468 mmol; Example 39), anhydrous toluene (0.5 mL), and then morpholine (0.053 mL, 0.61 mmol). Tris(dibenzylideneacetone)-dipalladium(0) (0.004 g, 0.0044 mmol), 2-(di-tert-butylphosphine)biphenyl (0.006 g, 0.020 mmol), and sodium tert-butoxide (0.063 g, 0.655 mmol) were added sequentially. The mixture was stirred at ambient temperature under a nitrogen atmosphere for 5 h and was poured into EtOAc (50 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated to a dark yellow oil. This crude product was purified using radial chromatography (EtOAc:hexanes 15:85 to 50:50) to give a yellow oil (0.058 g, 19%). 1H NMR (400 MHz, CDCl3) 1.07-1.18 (m, 3H), 1.29-1.40 (m, 1H), 1.42 (s, 9H), 1.52-1.70 (m, 4H), 1.91-1.93 (m, 2H), 2.34 (s, 3H), 2.46 (t, J=8.1 Hz, 2H), 2.87 (t, J=7.8 Hz, 2H), 2.94 (t, J=6.8 Hz, 2H), 3.24 (t, J=4.9 Hz, 4H), 3.48-3.50 (m, 1H), 3.86 (t, J=4.9 Hz, 4H), 4.20 (t, J=6.6 Hz, 2H), 5.07 (s, 2H), 6.79 (dd, J=8.6, 2.7 Hz, 1H), 6.85-6.93 (m, 3H), 7.09 (d, J=8.3 Hz, 1H), 7.87 (dd, J=11.5, 2.7 Hz, 2H). MS (ES) m/e 648 (M+1).

Provenance & Evidence