Trifluoroacetic acid → (+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoic acid

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Reaction Steps

A stirred solution of (±)-t-butyl 3-(3-cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoate [0.5 g, Reference Example 1(a)] in dichloromethane (20 ml), at 0° C., was treated with trifluoroacetic acid (4 ml). The solution was allowed to warm to room temperature and then stirred for 18 hours. The reaction mixture was evaporated and the brown residue subjected to flash chromatography on silica eluting with a mixture of petroleum ether and ethyl acetate (1:1, v/v) to give the title compound (0.4 g) as a colourless oil. NMR (CDCl3): δ1.60 (m,8H), 1.90 (m,6H), 2.60 (m,4H), 3.28 (m,1H), 3.82 (s,3H), 4.74 (m,1H), 6.78 (d,1H), 7.00-7.38 (m,7H). Mass spectrum (FAB): m/z 428 M+.

Provenance & Evidence