Trifluoroacetic acid → 5-Biphenyl-4-yl-3-hydroxy-2-methyl-pentanoic acid

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Reaction Steps

A solution of trifluoroacetic acid in dichloromethane (20%; 10 mL) was added to 5-biphenyl-4-yl-2-methyl-3-oxo-pentanoic acid tert-butyl ester (Intermediate 7, 130 mg, 0.382 mmol) and the resulting solution stirred at room temperature for 1.5 hour. The volatiles were evaporated under reduced pressure and the residue was purified by column chromatography on silica gel (1:2 ethyl acetate: 40–60 petroleum ether) to give the title compound (60 mg, 56%) as a white solid, mixture of diastereoisomers. LC/MS: 3.22 min; z/e 302, calcd (M+NH4) 302. 1H NMR (400 MHz: CDCl3): 7.59 (2 H), 7.51 (2 H), 7.40 (2 H), 7.28 (3 H), 4.21, 4.01 3.75, 2.91, 2.76, 2.62, 1.88, 1.25.

Provenance & Evidence