3-{4-[4-(Tert-butoxycarbonylaminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acid → 3-{4-[4-(Aminodimethylcarbamoylmethyl)-phenoxy]-phenyl}-propionic acid

Participants

Reaction Conditions

Reaction Steps

The acid compound 33 (0.3 g) was dissolved in CH2Cl2 (20 mL) and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 20 min. The bubbling was discontinued and the reaction mixture was stirred at room temp for 1 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×25 mL), decanted, and dried to yield the desired compound 37 as a white amorphous solid (0.15 g, 59%). 1H NMR (400 MHz, DMSO-d6): 12.2 (br, 1H), 7.47 (d, J=9.2 Hz, 2H), 7.29 (d, J=8.4 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 6.96 (d, J=8.4 Hz, 2H), 5.49 (s, 1H), 2.90 (s, 3H), 2.81-2.84 (m, 5H), 2.54 (t, J=8.0 Hz, 2H).

Provenance & Evidence