Potassium Hydroxide → HCID 67250298, compound

HRID 1183997Notes

Reaction equation

HRID 1183997 reaction equation
[OH-].[K+].[F:3][C:4]1[C:5](=[O:29])[N:6]([CH2:16][CH2:17][C@@:18]([CH3:28])([S:24]([CH3:27])(=[O:26])=[O:25])[C:19]([O:21]CC)=[O:20])[CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1.CO.O>[F:3][C:4]1[C:5](=[O:29])[N:6]([CH2:16][CH2:17][C@@:18]([CH3:28])([S:24]([CH3:27])(=[O:25])=[O:26])[C:19]([OH:21])=[O:20])[CH:7]=[CH:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67248709Ethyl (2R)-4-(3-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 67250298HCID 67250298, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Potassium hydroxide (120 mg, 2.14 mmol) was added to a solution of ethyl (2R)-4-(3-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate (131 mg, 0.33 mmol) in THF:methanol:water (2:2:1, 10 mL) and the reaction was stirred at RT overnight. The reaction was concentrated, and the residue was dissolved in aqueous 1N sodium hydroxide (20 mL), washed with ethyl acetate (3×20 mL), acidified using concentrated HCl, and extracted with ethyl acetate (3×50 mL). The combined organics were dried (MgSO4), filtered, and concentrated to afford the title compound as a white solid (88.4 mg, 72.7%). LC-MS m/z 383.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.59 (s, 3H) 2.13-2.30 (m, 1H) 3.17 (s, 3H) 3.93-4.23 (m, 2H) 6.43 (t, J=6.93 Hz, 1H) 7.44-7.56 (m, 3H) 7.57-7.66 (m, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in aqueous 1N sodium hydroxide (20 mL)
  3. washwashed with ethyl acetate (3×20 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-293250bfe4234b3abe40140be7191f6b
Source dataset
uspto-grants-2014_03
Patent number
US08664401B2

Reaction notes

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