Electrophilic substitution in highly substituted diphenyl ethers

Abstract

Hamilton and Blanchard mp 128-130°; [a] 26d +23.8°(c 1.0); ir bands (CHClj) at 3510 and 1715 cm-1; nmr signals (CC1<) at 5.9 m (H-7), 4.0 m (H-12, simplifies on D20 exchange), 3.51 (methoxyl), 3.25 (H-14), 2.25 d (J = 10 Hz, -OH, disappears on D20 exchange), 1.21 (C-4 methyl), 1.01 d and 0.94 d {J = 7 Hz, isopropyl methyls), and 0.74 ppm (C-10 methyl); mass spectrum 348 (molecular ion).

Thyroxine analogs. 22. Thyromimetic activity of halogen-free derivatives of 3,5-dimethyl-L-thyronine

“…7V-Acetyl-2-(3-isopropyl-4-methoxyphenyl)-3,5-dimethyl-DLtyrosine ethyl ester (14) was previously prepared and reported as DL-10:4a ir (KBr pellet) 3455 cm-1 (phenolic OH); uv Xmax (EtOH) 276, 282 s U 3300); Xmax (EtOH, OH') 300 (e 4000); tic (uv) fif(fll) 0.33; nmr (DCC13) ó 1.17 (t, J = 7.5 Hz, 3 H. Et-CH3), 1.23 (d, J = 6.0 Hz, 6 H, ¿-Pr-CH3), 1.90 (s, 3 H, Ac-CH3), 1.92 (s. 3 H, Ar-CHa), 2.28 (s. 3 H, Ar-CH3), 2.70 (4, 2 H, 3-CH2), 3.40 (7, 1 H, ¿-Pr-CH), 3.92 (s. 3 H, 0-CH3). 4.08 (q. J = 7.5 Hz, 2 H. Et-CH2), 4.58 (m, 1 H, -CH), 5.0 (s, 1 H, OH), 5.65 (d, J = 6 Hz, H, NH), 7.00 (br s, 3 H, Ar-H), 7.07 (br s. 1 H. Ar-H); Cl mass spectrum [MH]+ 428.…”