p-Toluenesulfonic acid → HCID 57326693, compound

HRID 1183998Notes

Reaction equation

HRID 1183998 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[F:12][C:13]1[C:14](=[O:43])[N:15]([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:16]=[CH:17][C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[F:12][C:13]1[C:14](=[O:43])[N:15]([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:16]=[CH:17][C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86671957HCID 86671957, compound

Product 1

HCID 57326693HCID 57326693, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyrinium p-toluenesulfonate (20 mg, 0.080 mmol) was added to a solution of (2R)-4-(3-fluoro-2-oxo-4-phenylpyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (110 mg, 0.236 mmol) in ethanol (5 ml) and heated at reflux for 3 hours. The solution was cooled to RT, and upon cooling, a solid precipitated. The solid was collected via filtration and washed with ethanol (5 mL), heptane (10 mL), and ether (10 mL). The solid was dried under vacuum to afford the title compound as a yellow solid (38.4 mg, 42.6%). LC-MS m/z 383.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.60 (s, 3H) 2.10-2.26 (m, 1H) 3.11 (s, 3H) 3.70-3.94 (m, 1H) 4.07-4.30 (m, 1H) 6.46 (t, J=6.93 Hz, 1H) 7.46-7.57 (m, 3H) 7.59-7.65 (m, 3H)

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureupon cooling
  4. customa solid precipitated
  5. filtrationThe solid was collected via filtration
  6. washwashed with ethanol (5 mL), heptane (10 mL), and ether (10 mL)
  7. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-22a53d96982d49e7864854ad5ada1e40
Source dataset
uspto-grants-2014_03
Patent number
US08664401B2

Reaction notes

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