Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 84295Notes

Reaction equation

HRID 84295 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[F:18][C:19]1[C:20]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:21][C:22](=[O:43])[N:23]([CH2:25][CH2:26][C@@:27]([CH3:42])([S:38]([CH3:41])(=[O:40])=[O:39])[C:28]([NH:30][O:31]C2CCCCO2)=[O:29])[CH:24]=1>C(O)C>[F:18][C:19]1[C:20]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:21][C:22](=[O:43])[N:23]([CH2:25][CH2:26][C@@:27]([CH3:42])([S:38]([CH3:41])(=[O:39])=[O:40])[C:28]([NH:30][OH:31])=[O:29])[CH:24]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86717774(2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 57326694(2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamideYield 52,734.102%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyridinium p-toluenesulfonate (22 mg, 0.088 mmol) was added to a solution of (2R)-4-(5-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (197 mg, 0.422 mmol). The solution was heated to reflux in ethanol (10 ml) and stirred at this temperature until complete. The solution was cooled to RT, and the volatiles were removed in vacuo. The solid was triturated in ethanol (5 mL), collected via filtration, then washed with ethanol (3×5 mL), hexanes (10 mL), and ether (3×10 mL). The solid was dried under vacuum to afford a white solid (85.1 g, 76.4%). LC-MS m/z 383.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58 (s, 3 H) 2.11-2.23 (m, 0 H) 2.41-2.55 (m, 1 H) 3.12 (s, 3 H) 3.73-3.84 (m, 1 H) 3.99-4.11 (m, 1 H) 6.53 (d, J=7.61 Hz, 1 H) 7.41-7.73 (m, 5 H) 8.04 (d, J=6.44 Hz, 1 H) 9.24 (s, 1 H) 11.10 (s, 1 H).

Workup

  1. temperatureThe solution was heated
  2. customthe volatiles were removed in vacuo
  3. customThe solid was triturated in ethanol (5 mL)
  4. filtrationcollected via filtration
  5. washwashed with ethanol (3×5 mL), hexanes (10 mL), and ether (3×10 mL)
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-9dc6d173b68345018c6891ed8fd11969
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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