Treatment of 4-(dimethylamino)benzoic acid (I) with thionyl chloride produced the corresponding acid chloride (II). Subsequent coupling of (II) with 4-tert-butyldimethylsilyloxy-N1-(4-methoxybenzoyl)-1,2-benzenediamine (III) yielded the bisamide (IV). Finally, desilylation of (IV) in the presence of HCl in aqueous THF afforded the title phenol compound.
Reduction of ethyl ester (I) with LiAlH4 provides primary carbinol (II), which is then converted into amine (III) by Mitsunobu reaction with phthalimide (A) in the presence of PPh3 and DEAD in THF, followed by an hydrazine mediated deprotection in EtOH. Reaction of amine (III) with 2-nitrophenyl isocyanate (IV) in CHCl3/THF or CH2Cl2, followed by reduction of the nitro group by hydrogenation over Pd/C in EtOH, affords aniline (V). Finally, aniline (V) is condensed with acid chloride (VI) in CHCl3 in the presence of pyridine to furnish the target compound.