Lithium Hydroxide → HCID 23508306, compound

HRID 413401Notes

Reaction equation

HRID 413401 reaction equation
[CH3:1][N:2]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH:3]1[CH2:7][CH:6]([CH2:8][S:9][C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[O:5][C:4]1=[O:19].[OH-:37].[Li+]>O.C1COCC1>[CH3:1][N:2]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)=[CH:25][CH:24]=1)(=[O:22])=[O:21])[CH:3]([CH2:7][CH:6]([OH:5])[CH2:8][S:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1)[C:4]([OH:19])=[O:37]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 23508289HCID 23508289, compound

Product 1

HCID 23508306HCID 23508306, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl 3-[(4′-Methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[[(2-benzothiazolyl)thio]methyl]-tetrahydrofuran 62c (1.00 g, 2.05 mmol) in water (5 mL) and THF (5 mL) is slowly added lithium hydroxide (0.49 g, 20.5 mmol). The reaction is stirred for 4 hr, then concentrated to dryness. The reaction mixture is diluted with water and then the mixture is extracted with ethy ether (2×25 mL) The ethyl ether layer is discarded and the aqueous layer is slowly acidified with 1N HCl to pH 5, and then extracted 3 times with ethyl acetate. The combined ethyl acetate layers are washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The white solid is then recrystallized with ethyl acetate/hexanes to give the desired product as a white solid.

Workup

  1. concentrationconcentrated to dryness
  2. additionThe reaction mixture is diluted with water
  3. extractionthe mixture is extracted with ethy ether (2×25 mL) The ethyl ether layer
  4. extractionextracted 3 times with ethyl acetate
  5. washThe combined ethyl acetate layers are washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe white solid is then recrystallized with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bf0e16f8c6a44c64b2e1d4c88f3b77d9
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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