3,4-Dimethylphenol → 3-{3-[3-(3,4-Dimethyl-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

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Reaction Steps

The title compound was prepared from 3-[3-(3-bromo-propoxy)-phenyl]-2-methoxy-propionic acid methyl ester (Example 323, Step 1) and 3,4-dimethylphenol via the same procedure used for the preparation of (2S)-2-methoxy-3-[4-(3-phenoxy-propoxy)-phenyl]-propionic acid (Example 285, Step 1). The enatiomers were separated by chiral HPLC. 1H-NMR (CDCl3, 200.15 MHz): 7.18 (d, 1H, J=7.5), 7.02 (d, 1H, J=8.3), 6.84–6.62 (m, 5H), 4.14 (t, 2H, J=6.4), 4.12 (t, 2H, J=5.9), 4.02 (dd, 1H, J=7.3, 4.0), 3.39 (s, 3H), 3.13 (dd, 1H, J=14.2, 4.6), 2.97 (dd, 1H, J=14.0, 7.5), 2.23 (q, 1H, J=6.2.1), 2.22 (s, 3H), 2.18 (s, 3H). MS (ES) for C21H26O5 [M+Na]+: 381.2.

Provenance & Evidence