Lithium hydroxide, monohydrate → HCID 67248550, compound

HRID 1475867Notes

Reaction equation

HRID 1475867 reaction equation
[CH3:1][C:2]([S:24]([CH3:27])(=[O:26])=[O:25])([CH2:8][CH2:9][N:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([CH3:22])[C:11]1=[O:23])[C:3]([O:5]CC)=[O:4].O.[OH-].[Li+]>O1CCCC1.CO.O.Cl>[CH3:1][C:2]([S:24]([CH3:27])(=[O:25])=[O:26])([CH2:8][CH2:9][N:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([CH3:22])[C:11]1=[O:23])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67248376ethyl 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoate

Product 1

HCID 67248550HCID 67248550, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoate (118.3 mg, 0.313 mmol) in tetrahydrofuran/methanol/water (4:1:1, 3.13 mL) was added lithium hydroxide monohydrate (26.3 mg, 0.626 mmol). The mixture was stirred at ambient temperature overnight. The mixture was diluted with aqueous HCl (1N in water) and extracted with ethyl acetate 2×. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to dryness to afford 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoic acid as a solid. 109.4 mg.

Workup

  1. extractionextracted with ethyl acetate 2×
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3a31da9812554639a6436c9e3cdbec1d
Source dataset
uspto-grants-2015_04
Patent number
US09018384B2

Reaction notes

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