Water → HCID 178477339, compound

HRID 265156Notes

Reaction equation

HRID 265156 reaction equation
[CH2:1]([S:3][C:4]1[N:5]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:6]([C:13]([O:15]CC)=[O:14])=[C:7]([C:9]([OH:12])([CH3:11])[CH3:10])[N:8]=1)[CH3:2].O.[OH-].[Li+].O>O1CCOCC1>[CH2:1]([S:3][C:4]1[N:5]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:6]([C:13]([OH:15])=[O:14])=[C:7]([C:9]([OH:12])([CH3:11])[CH3:10])[N:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 178468946HCID 178468946, compound

Product 1

HCID 178477339HCID 178477339, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.00 g of ethyl 2-ethylthio-4-(1-hydroxy-1-methylethyl)-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in Example 107(b)] and 256 mg of lithium hydroxide monohydrate were added to a mixture of 10 ml of water and 10 ml of dioxane. The mixture was then stirred at room temperature for 24 hours after which it was concentrated by evaporation under reduced pressure. The resulting residue was dissolved in water, and then 6.1 ml of 1N aqueous hydrochloric acid were added. The oily matter which appeared was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure, to give 955 mg of the title compound as an amorphous powder.

Workup

  1. concentrationwas concentrated by evaporation under reduced pressure
  2. dissolutionThe resulting residue was dissolved in water
  3. addition6.1 ml of 1N aqueous hydrochloric acid were added
  4. extractionThe oily matter which appeared was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-952502556fa2402f8c376edb8ab218a0
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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