Lithium hydroxide, monohydrate → HCID 67250346, compound

HRID 84271Notes

Reaction equation

HRID 84271 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]([CH3:27])([S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([O:20]CC)=[O:19])[C:11](=[O:28])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.CO.O.Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]([CH3:27])([S:23]([CH3:26])(=[O:24])=[O:25])[C:18]([OH:20])=[O:19])[C:11](=[O:28])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67249611Ethyl 4-(4-(benzyloxy)-2-oxopyridin-1(2h)-yl)-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 67250346HCID 67250346, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 4-[4-(benzyloxy)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanoate (740 mg, 1.82 mmol) in tetrahyrofuran/methanol/water (4:1:1, 18.2 mL) was added lithium hydroxide monohydrate (152 mg, 3.63 mmol). The mixture was stirred at ambient temperature overnight. The mixture was diluted with aqueous HCl (1N in water) and extracted with ether 2×. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated to dryness to afford 4-[4-(benzyloxy)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanoic acid as a solid. 674.9 mg.

Workup

  1. extractionextracted with ether 2×
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1243e281694d4abbb851a0603c12b8c5
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

Loading…