Ethanol → HCID 118113302, compound

HRID 1485129Notes

Reaction equation

HRID 1485129 reaction equation
[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]([C:18](=[O:31])CC(NCC(OC(C)(C)C)=O)=O)[C:9]2(C(OC)=O)[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1.[C:38](=[O:41])([O-])[O-:39].[Cs+].[Cs+].[CH2:44]([OH:46])[CH3:45]>>[C:1]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[C:9]3([CH2:10][CH2:11][CH2:12][CH2:13]3)[C:44]([OH:46])=[C:45]([C:18]([NH:8][CH2:7][C:38]([OH:39])=[O:41])=[O:31])[C:18]2=[O:31])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 10796Cesium carbonateHCID 118113267HCID 118113267, compound

Product 1

HCID 118113302HCID 118113302, compound

Procedure

To a solution in ethanol (5.31 mL) of the compound (270 mg) obtained in step (1) above, cesium carbonate (346 mg) was added and the mixture was stirred at room temperature for an hour. The reaction mixture was concentrated under reduced pressure and 1 mol/L hydrochloric acid was added to the resulting residue. Extraction was conducted with ethyl acetate and the combined organic layers were dried over anhydrous sodium sulfate. After removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. To a solution of the resulting concentrate (253 mg) in chloroform (4.88 mL), trifluoroacetic acid (2.44 mL) was added and the mixture was stirred at room temperature for 15 hours. After concentrating under reduced pressure, the residue was recrystallized with a liquid mixture of n-hexane and ethyl acetate and the precipitate was recovered by filtration to give the titled compound as a colorless solid (335 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and 1 mol/L hydrochloric acid
  2. additionwas added to the resulting residue
  3. extractionExtraction
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. customAfter removing the
  6. filtrationdesiccant by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. concentrationTo a solution of the resulting concentrate (253 mg) in chloroform (4.88 mL)
  9. additiontrifluoroacetic acid (2.44 mL) was added
  10. stirringthe mixture was stirred at room temperature for 15 hours
  11. concentrationAfter concentrating under reduced pressure
  12. customthe residue was recrystallized with a liquid mixture of n-hexane and ethyl acetate
  13. filtrationthe precipitate was recovered by filtration

Sources & evidence

ORD record
ord-dff1497797ed40848df9a2685db64b3a
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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