HCID 20827007, compound → HCID 22280028, compound

Participants

Reaction Steps

Preparation of [4-(4-tert-Butyl-benzyloxy)-phenyl]-methanol (compound 34A) The title compound was prepared in the manner analogous to Example 14A using 1-bromomethyl-4-tert-butyl-benzene and 4-hydroxymethyl-phenol. MS m/z 253 (M-OH). Step 2. Preparation of 4-tert-Butyl-1-(4-chloromethyl-phenoxymethyl)-benzene (compound 34B) The title compound was prepared in the manner analogous to Example 3B using 34A. MS m/z 253 (M-Cl). Step 3. Preparation of {4-[4-(4-tert-Butyl-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid methyl ester (compound 34C) The title compound was prepared in the manner analogous to Example 1F using 34B and 2C. MS m/z 465 (M+1). Step 4. Preparation of {4-[4-(4-tert-Butyl-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid (compound 34) The title compound was prepared in the manner analogous to Example 1 using 34C. mp 135-137° C.; IR (KBr) cm−1: 2961, 2908, 1751, 1495, 1233, 1194; 400 MHz 1H NMR (DMSO-d6): δ 13.00 (br(s), 1H), 7.27-7.38 (m, 4H), 7.02-7.17 (m, 4H), 6.82-6.88 (m, 2H), 6.69 (d, 1H, J=8.5 Hz), 4.96 (s, 2H), 4.61 (s, 2H), 3.99 (s, 2H), 2.08 (s, 3H), 1.22 (s, 9H); MS m/z 451 (M+1). Anal. Calc'd for C27H30O4S: C, 71.97; H, 6.71; found: C, 71.66; H, 6.52.

Provenance & Evidence