Trifluoroacetic acid → (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-methoxy-ethyl)-12-oxo-nonadec-4-enoic acid

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Reaction Steps

No. 5534988, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-methoxy-ethyl)-undec-4-enoate (21.5 g, 28.2 mmol) was dissolved in dichloromethane (215 mL), and trifluoroacetic acid (215 mL) was added. The mixture was stirred at room temperature for 2 hours. After confirming the consumption of the starting materials by LCMS, the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue, which was washed with water, an aqueous solution of 2% NaHCO3 (to about pH 7.3), water, a saturated aqueous solution of ammonium chloride, and a saturated brine, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified with SP1 (Diol cartridge, 50% ethyl acetate/n-hexane, Rf=0.4) to obtain No. 5444958, (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-methoxy-ethyl)-12-oxo-nonadec-4-enoic acid (11.1 g, 61% yield, white powder).

Provenance & Evidence