Hydrochloric Acid → 6-[3-(1,3,3-Trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic Acid

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Reaction Conditions

Reaction Steps

To a solution of 6-[3-(1,3,3-trimethyl-2-oxo-2,3-dihydro-1H-indol-6-yloxymethyl)-phenyl]-hexanoic acid methyl ester (110 mg, 0.27 mmol) in (1:1) THF/CH3OH (1 mL) is added 250 μL water and 10N NaOH soln (270 μL). The mixture is stirred for 16 hrs, cooled to 5° C., adjusted to pH 4 with 2N HCl soln. and diluted with EtOAc. The organic layer is washed with brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 50% ethyl acetate/5% methanol/hexanes) to give 67 mg of title compound. 1H NMR (300 MHz, CDCl3) δ 7.29 (m, 3H), 7.14 (d, 1H), 7.09 (d, 1H), 6.63 (dd, 1H), 6.52 (d, 1H), 5.04 (s, 2H), 3.18 (s, 3H), 2.64 (t, 2H), 2.36 (t, 2H), 1.66 (m, 4H), 1.40 (m, 2H), 1.34 (s, 6H). MS (ESI) 396 (M+H)+.

Provenance & Evidence