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

HRID 413369Notes

Reaction equation

HRID 413369 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]3[CH2:23][CH:22]([CH2:24][S:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:21][C:20]3=[O:33])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH2:34].[OH-].[Li+]>O.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([NH:18][CH:19]([CH2:23][CH:22]([OH:34])[CH2:24][S:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]([OH:21])=[O:33])(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 235082703-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(benzylthio)methyl]-tetrahydrofuran

Product 1

HCID 99357792-[(4'-Methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4-hydroxy-5-(benzylthio)-pentanoic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(benzylthio)methyl]-tetrahydrofuran 17a (40 mg, 0.083 mmol) in water (3 mL) and THF (3 mL) is added slowly lithium hydroxide monohydrate (35 mg, 0.82 mmol). The reaction mixture is stirred overnight, 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 (1:4) to give the desired product as a white solid.

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 (1:4)

Sources & evidence

ORD record
ord-e17cb121664642bd8fe7129f80e103f3
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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