Lithium hydroxide, monohydrate → 2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanoic acid

HRID 2405952Notes

Reaction equation

HRID 2405952 reaction equation
[CH3:1][C:2]([S:21]([CH3:24])(=[O:23])=[O:22])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]=[CH:11]1)[C:3]([O:5]CC)=[O:4].O.[OH-].[Li+]>C1COCC1.CO.O.Cl>[CH3:1][C:2]([S:21]([CH3:24])(=[O:22])=[O:23])([CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]=[CH:11]1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 70818083ethyl 2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanoate

Product 1

HCID 708175182-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanoic acidYield 98.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanoate (335 mg, 0.956 mmol, 1 eq) in THF/MeOH/Water (4:1:1) was added lithium hydroxide monohydrate (160 mg, 3.82 mmol, 4 eq) and the mixture was allowed to stir at RT overnight. The reaction was diluted with 1 N HCl and loaded onto a 6 g MCX column. The column was washed with 1 column volume water and 2 column volumes MeOH. The washes were discarded. The column was then eluted with 0.5 N NH3 in Methanol. The eluant was concentrated to give 2-methyl-2-(methylsulfonyl)-4-(4-phenyl-1H-imidazol-1-yl)butanoic acid (304 mg, 98% yield). LC-MS M+H+323.4.

Workup

  1. washThe column was washed with 1 column volume water and 2 column volumes MeOH
  2. washThe column was then eluted with 0.5 N NH3 in Methanol
  3. concentrationThe eluant was concentrated

Sources & evidence

ORD record
ord-9e976bdb36344793b557019b094a55e0
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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