Lithium hydroxide, monohydrate → 2-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4-hydroxy-5-(phenylthio)-pentanoic Acid

HRID 413367Notes

Reaction equation

HRID 413367 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]2[CH2:15][CH:14]([CH2:16][S:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:13][C:12]2=[O:24])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH2:31].[OH-].[Li+]>O.C1COCC1>[C:1]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][CH:11]([CH2:15][CH:14]([OH:31])[CH2:16][S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]([OH:13])=[O:24])(=[O:8])=[O:9])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 235082763-[[(1,1'-Biphenyl)-4-yl]sulfonyl]amino-2-oxo-5-[(phenylthio)methyl]-tetrahydrofuran

Product 1

HCID 235082932-[[(1,1'-biphenyl)-4-yl]sulfonyl]amino-4-hydroxy-5-(phenylthio)-pentanoic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[[(1,1′-biphenyl)-4-yl]sulfonyl]amino-2-oxo-5-[(phenylthio)methyl]-tetrahydrofuran 16c (0.18 g, 0.41 mmol) in water (5 mL) and THF (5 mL) is added slowly lithium hydroxide monohydrate (172 mg, 4.1 mmol). The reaction mixture is stirred for 3 hr, then concentrated to dryness. The resulting mixture is diluted with water, and then the mixture is extracted twice with Et2O. The Et2O layer is discarded and the aqueous layer is neutralized carefully with 1N HCl to pH 6, then extracted three times with EtOAc. The combined EtOAc layer is washed with brine, dried over MgSO4 and concentrated to a solid which is recrystallized from EtOAc/hexane to give the desired product.

Workup

  1. concentrationconcentrated to dryness
  2. additionThe resulting mixture is diluted with water
  3. extractionthe mixture is extracted twice with Et2O
  4. extractionextracted three times with EtOAc
  5. washThe combined EtOAc layer is washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to a solid which
  8. customis recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-13b309a7b7924ea8a1be973783ef8c5a
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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