Acetic Acid → HCID 46830910, compound

HRID 1691793Notes

Reaction equation

HRID 1691793 reaction equation
C(O)(=O)C.C1COCC1.[Br:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([O:18][CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C)=[CH:13][C:12]=1[CH2:29][C:30]([N:32]1[CH:37]=[CH:36][C:35](=[O:38])[CH2:34][CH:33]1[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1)=[O:31]>O>[Br:10][C:11]1[CH:16]=[C:15]([F:17])[C:14]([O:18][CH2:19][CH2:20][OH:21])=[CH:13][C:12]=1[CH2:29][C:30]([N:32]1[CH:37]=[CH:36][C:35](=[O:38])[CH2:34][C@H:33]1[C:39]1[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=1)=[O:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 66906497HCID 66906497, compound

Product 1

HCID 46830910HCID 46830910, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of acetic acid (4.5 ml), water (1.5 ml) and THF (1.5 ml) was added to a flask containing 1-(2-{2-bromo-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-4-fluoro-phenyl}-acetyl)-2-(4-fluoro-phenyl)-2,3-dihydro-1H-pyridin-4-one (0.048 g, 0.082 mmol). The mixture was stirred at room temperature for 16 hours. Water was added and the product was extracted with EtOAc. The extract was washed with water and brine, dried over MgSO4, filtered and concentrated to dryness. Purification by flash chromatography (EtOAc) gave (S)-1-{2-[2-bromo-4-fluoro-5-(2-hydroxy-ethoxy)-phenyl]-acetyl}-2-(4-fluoro-phenyl)-2,3-dihydro-1H-pyridin-4-one (0.032 g) as a white foam.

Workup

  1. additionwas added to a flask
  2. extractionthe product was extracted with EtOAc
  3. washThe extract was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customPurification by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-410ee367d0c648f2823f5fcbdbc4783a
Source dataset
uspto-grants-2012_04
Patent number
US08153808B2

Reaction notes

Loading…