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

HRID 2122024Notes

Reaction equation

HRID 2122024 reaction equation
C[O:2][C:3](=[O:32])[C@H:4]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@H:5]([S:12][CH2:13][CH3:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[I-].[Li+]>N1C=CC=CC=1>[CH2:13]([S:12][C@H:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C@@H:4]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:3]([OH:32])=[O:2])[CH3:14]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 69881323(2S,3R)-3-Ethylsulfanyl-2-(4'-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic acid methyl ester

Product 1

HCID 9825456(2S,3R)-3-Ethylsulfanyl-2-(4'-fluoro-biphenyl-4-sulfonylamino)-3-phenyl-propionic Acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(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.

Workup

  1. temperatureis refluxed under argon overnight
  2. custompartitioned between ethyl acetate and 1.0 N aq. HCl
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by reverse phase preparative HPLC (gradient elution, 0.1% aq. trifluoroacetic acid/acetonitrile)

Sources & evidence

ORD record
ord-00de4756a0cc440f803f2a4c4dc38425
Source dataset
uspto-grants-2004_02
Patent number
US06696456B1

Reaction notes

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