Hydroxyphenylacetic acid → HCID 68535772, compound

Participants

Reaction Steps

4-Hydroxyphenyl acetic acid (1.55 g, 10.2 mmol), 4-ethyl-phenylamine (1.28 ml, 10.3 mmol), TBTU (4.82 g, 15 mmol), and NMM (8.79 ml, 80 mmol) are stirred in DMF (30 ml) at rt for 5 h. The reaction mixture is taken up in AcOEt (0.2 L), washed with H2O (40 ml, 2×) and brine (40 ml, 2×), dried (Na2SO4), concentrated under reduced pressure, and flash chromatographed (silica gel, 3.5×25 cm, AcOEt/hexane=1:2→2:3) giving the title compound of Stage 16.1 as a colorless solid (1.68 g, 6.59 mmol; 66%) M+H=256.1; 1H-NMR (400 MHz, DMSO-d6): 10.0/9.24 (s/s, 1H, NH/OH), 7.46 (d, 8.5 Hz, 2H, phenyl), 7.09 (d, 8.5 Hz, 4H, phenyl), 6.66 (d, 8.5 Hz, 2H, phenyl), 3.47 (s, 2H, aryl-CH2), 2.53 (qu, 7.5 Hz, 2H, CH2), 1.13 (t, 7.5 Hz, 3H, CH3); R. (AcOEt/hexane=1:1): 0.66; m.p. =146-148° C.

Provenance & Evidence