Water → HCID 58677627, compound

HRID 1012614Notes

Reaction equation

HRID 1012614 reaction equation
[Cl:1][C:2]1[CH:28]=[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[F:37])[CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([NH:13][C:14](=[O:24])[NH:15][CH2:16][CH2:17][O:18]C(=O)C(C)=C)[CH:9]=[CH:10][C:11]=1[CH3:12])=[O:5].[OH-].[Na+].C([O-])(O)=O.[Na+].O>CCO.CCOC(C)=O>[Cl:1][C:2]1[CH:28]=[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[F:37])[CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([NH:13][C:14]([NH:15][CH2:16][CH2:17][OH:18])=[O:24])[CH:9]=[CH:10][C:11]=1[CH3:12])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 58677504HCID 58677504, compound

Product 1

HCID 58677627HCID 58677627, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 259 (0.05 g, 0.095 mmol) was dissolved in EtOH (2.5 mL). 2 N NaOH (0.25 mL) was added and the solution was heated to reflux for 3 h. The reaction mixture was cooled to room temperature and saturated aqueous NaHCO3 (2 mL) was added. H2O and EtOAc were added and the phases were separated. The water phase was extracted with EtOAc. The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc as the eluent. This afforded the title compound as a slightly coloured solid. 13C NMR (CD3OD) δ

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3 h
  3. customthe phases were separated
  4. extractionThe water phase was extracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-dcd711d22e684deeaf7c946f01d6349c
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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