p-Toluenesulfonic acid → HCID 57326693, compound

HRID 84290Notes

Reaction equation

HRID 84290 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, 3 H) 2.10-2.26 (m, 1 H) 3.11 (s, 3 H) 3.70-3.94 (m, 1 H) 4.07-4.30 (m, 1 H) 6.46 (t, J=6.93 Hz, 1 H) 7.46-7.57 (m, 3 H) 7.59-7.65 (m, 3 H)

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-1a0eb0287125433b83ff668985aba2e8
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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