Hydrochloric Acid → 2-Ethyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanoic acid

HRID 84283Notes

Reaction equation

HRID 84283 reaction equation
[OH-].[K+].[CH2:3]([C:5]([S:26]([CH3:29])(=[O:28])=[O:27])([CH2:11][CH2:12][N:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][C:14]1=[O:25])[C:6]([O:8]CC)=[O:7])[CH3:4].O1CCCC1CO.O.Cl>O>[CH2:3]([C:5]([S:26]([CH3:29])(=[O:28])=[O:27])([CH2:11][CH2:12][N:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][C:14]1=[O:25])[C:6]([OH:8])=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66577907Tetrahydrofuran-methanol waterHCID 67248458Ethyl 2-ethyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanoate

Product 1

HCID 672483492-Ethyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium hydroxide (37 mg, 0.66 mmol, 6.0 equiv) was added to a solution of ethyl 2-ethyl-2-(methylsulfonyl)-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanoate (43 mg, 0.11 mmol, 1.0 equiv) in 2:2:1 tetrahydrofuran-methanol-water (2.5 mL) at 0° C. The reaction was allowed to warm to room temperature and stir overnight. The reaction was concentrated under reduced pressure to provide a wet residue that was diluted with water (5 mL) and acidified (to pH=2) with 1.0 hydrochloric acid. The resulting white precipitate was filtered, washed with water, and dried under reduced pressure to provide the title compound (34 mg, 85%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.09 (t, J=7.52 Hz, 3 H) 1.42 (s, 3 H) 1.93-2.07 (m, 1 H) 2.23-2.37 (m, 2 H) 2.55 (d, J=5.66 Hz, 1 H) 3.25 (s, 3 H) 4.10-4.24 (m, 2 H) 4.47-4.59 (m, 2 H) 6.63-6.67 (m, 1 H) 6.90 (d, J=1.95 Hz, 1 H) 7.44-7.50 (m, 4 H) 7.54-7.62 (m, 2 H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto provide a wet residue that
  3. filtrationThe resulting white precipitate was filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-6766f268efde4e358b93e18b87584ab9
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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