Lithium hydroxide, monohydrate → HCID 178488636, compound

HRID 413372Notes

Reaction equation

HRID 413372 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][C:26]4[N:30]=[CH:29][NH:28][N:27]=4)[O:21][C:20]3=[O:31])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH2:32].[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:32])[CH2:24][S:25][C:26]3[N:30]=[CH:29][NH:28][N:27]=3)[C:20]([OH:21])=[O:31])(=[O:16])=[O:17])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178488635HCID 178488635, compound

Product 1

HCID 178488636HCID 178488636, compound

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-[(1H-1,2,4-triazol-3-ylthio)methyl]-tetrahydrofuran 20a (0.34 g, 0.68 mmol) in water (5 mL) and THF (5 mL) is added slowly lithium hydroxide monohydrate (290 mg, 4.2 mmol). The reaction mixture is stirred for 4 h, then concentrated to dryness. Diluted with water, 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. additionDiluted 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-321808d888b64a52b71a97facddfcfaf
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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