Hydrochloric Acid → (2R)-4-{5-Fluoro-4-[4-(methylthio)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoic acid

HRID 468627Notes

Reaction equation

HRID 468627 reaction equation
O.[OH-].[Li+].[F:4][C:5]1[C:6]([C:25]2[CH:30]=[CH:29][C:28]([S:31][CH3:32])=[CH:27][CH:26]=2)=[CH:7][C:8](=[O:24])[N:9]([CH2:11][CH2:12][C@@:13]([CH3:23])([S:19]([CH3:22])(=[O:21])=[O:20])[C:14]([O:16]CC)=[O:15])[CH:10]=1.Cl>C1COCC1.O>[F:4][C:5]1[C:6]([C:25]2[CH:26]=[CH:27][C:28]([S:31][CH3:32])=[CH:29][CH:30]=2)=[CH:7][C:8](=[O:24])[N:9]([CH2:11][CH2:12][C@@:13]([CH3:23])([S:19]([CH3:22])(=[O:21])=[O:20])[C:14]([OH:16])=[O:15])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86670638Ethyl (2R)-4-{5-fluoro-4-[4-(methylthio)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 70664819(2R)-4-{5-Fluoro-4-[4-(methylthio)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide monohydrate (165 mg, 6.68 mmol) was added to a solution of ethyl (2R)-4-{5-fluoro-4-[4-(methylthio)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoate (0.492 g, 1.12 mmol) in THF:water (1:1, 14 mL) and the reaction was allowed to stir at rt for 18 h. The reaction mixture was acidified using 4 M aq HCl to afford a precipitate. The solid was collected via filtration and dried under vacuum to afford the title compound as a solid (339 mg, 73%). MS (LCMS) m/z 414.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54 (s, 3H) 2.17 (ddd, J=13.42, 10.00, 5.07 Hz, 1H) 2.41-2.45 (m, 1H) 2.49 (s, 3H), 3.14 (s, 3H) 3.78-4.15 (m, 2H) 6.46 (d, J=7.81 Hz, 1H) 7.28-7.39 (m, 2H) 7.43-7.55 (m, 2H) 8.01 (d, J=6.83 Hz, 1H).

Workup

  1. customto afford a precipitate
  2. filtrationThe solid was collected via filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-eb0020bc67e547cdb5cd169dd3a66302
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

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