Methanesulfonyl chloride → Trifluoromethanesulfonic acid 6-methanesulfonyloxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester

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Reaction Steps

Suspend trifluoro-methanesulfonic acid 6-hydroxy-1-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-naphthalen-2-yl ester (12.5 g, 24 mmol) in dry methylene chloride (100 ml). Add diisopropylethylamine (8.3 mL, 48 mmol). Slowly add methanesulfonyl chloride (2.7 mL, 36 mmol). Pour the reaction into saturated aqueous sodium bicarbonate after 20 minutes and extract with methylene chloride. Wash the organic layer with water, dry with sodium sulfate, filter and concentrate in vacuo to yield 14.2 g (99%) of the title compound as an amber foam. 1H NMR (CDCl3) δ8.05 (d, J-=9.2 Hz, 1H), 7.90 (d, J=1.9 Hz, 1H), 7.76 (d, J=8.2 Hz, 2H), 7.75 (d, J=9.0 Hz, 1H), 7.59 (d, J=9.2 Hz, 1H), 7.43 (dd, J=9.2, 1.7 Hz, 1H), 6.94 (d, J=8.2 Hz, 2H), 4.17 (t, J=5.7 Hz, 2H), 3.23 (s, 3H), 2.79 (t, J=5.2 Hz, 2H), 2.5 (bs, 4H), 1.63-1.57 (m, 4H), 1.48-1.40 (m, 2H); LCMS mass spectrum (ion spray): m/z=602.3 (M+H).

Provenance & Evidence