Hydrochloric Acid → (S)-5,5-dimethyl-3-(4-(2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)phenyl)-4-phenyloxazolidin-2-one

HRID 525334Notes

Reaction equation

HRID 525334 reaction equation
F[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C@@H:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17]([CH3:26])([CH3:25])[O:16][C:15]3=[O:27])=[CH:10][CH:9]=2)=[CH:6][C:5]([C:28]2[N:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[CH:4][N:3]=1.[O:34]1CCOCC1.Cl>O>[CH3:25][C:17]1([CH3:26])[O:16][C:15](=[O:27])[N:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]3[C:2](=[O:34])[NH:3][CH:4]=[C:5]([C:28]4[N:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[CH:6]=3)=[CH:9][CH:10]=2)[C@H:18]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71736212(S)-3-(4-(2-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Product 1

HCID 71736384(S)-5,5-dimethyl-3-(4-(2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)phenyl)-4-phenyloxazolidin-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A resealable tube was charged with (S)-3-(4-(2-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.034 g, 0.077 mmol), dioxane (2.0 mL), and water (0.667 mL). Concentrated HCl (37%) (0.167 mL) was added, the system was flushed with argon, the tube was sealed, and the reaction mixture was stirred at 100° C. for 1.5 hours. The reaction mixture was next partitioned between EtOAc and saturated aqueous NaHCO3 solution. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford (S)-5,5-dimethyl-3-(4-(2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)phenyl)-4-phenyloxazolidin-2-one (0.034 g, 0.078 mmol, 100% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92 (s, 3H), 1.65 (s, 3H), 5.48 (s, 1H), 7.18-7.45 (m, 6H), 7.48-7.59 (m, 2H), 7.65-7.75 (m, 2 H), 8.32 (d, J=2.45 Hz, 1H), 8.43 (d, J=2.54 Hz, 1H), 8.80 (d, J=4.89 Hz, 2H), 12.13 (br. s., 1H). m/z (ESI) 439 (M+H)+.

Workup

  1. customthe system was flushed with argon
  2. customthe tube was sealed
  3. customThe reaction mixture was next partitioned between EtOAc and saturated aqueous NaHCO3 solution
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0fb40dbfc0ef4899b440359a3edbb262
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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