Lithium iodide → (2S,3R)-3-Ethylsulfanyl-2-(4'-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic Acid

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Reaction Steps

(2S,3R)-3-Ethylsulfanyl-2-(4′-fuoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic acid. A mixture of (2S, 3R)-3-ethylsulfanyl-2-(4′-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic acid methyl ester 4b (28 mg, 0.059 mmol) and lithium iodide (105 mg, 0.785 mmol) in pyridine (3 mL) is refluxed under argon overnight. The mixture is cooled to room temperature and partitioned between ethyl acetate and 1.0 N aq. HCl. The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by reverse phase preparative HPLC (gradient elution, 0.1% aq. trifluoroacetic acid/acetonitrile) to give the desired product as a pale orange solid.

Provenance & Evidence