Potassium Carbonate → HCID 59997913, compound

HRID 2211693Notes

Reaction equation

HRID 2211693 reaction equation
[O:1]=[S:2]1(=[O:35])[C:7](C(=O)C(F)(F)F)=[CH:6][N:5]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[O:22][C:21]3=[O:34])=[CH:16][CH:15]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+]>CO.C(#N)C>[O:35]=[S:2]1(=[O:1])[CH:3]=[CH:4][N:5]([C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:30])[CH3:31])[O:22][C:21]3=[O:34])=[CH:18][CH:19]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59997906HCID 59997906, compound

Product 1

HCID 59997913HCID 59997913, compound

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Procedure

The crude sulfone prepared in Step 6 (6.7 mmol) is suspended in 220 mL of MeOH-acetonitrile (2:1) and heated to reflux. Solid K2CO3 (3.4 g, 25 mmol) is then added, and the mixture stirred at reflux for 2 h. Upon cooling, the solution is filtered and the filtrate concentrated. The residue is dissolved in 50 mL of EtOAc—2.5% aq. NaHCO3 (1:1), the layers separated, and the aqueous phase extracted with more ethyl acetate. The combined organic layers are washed with brine and dried (MgSO4), filtered and concentrated. The resulting crude product is purified by column chromatography (0–2% MeOH—CH2Cl2) provided the title compound as a foam.

Workup

  1. temperatureheated to reflux
  2. temperatureat reflux for 2 h
  3. temperatureUpon cooling
  4. filtrationthe solution is filtered
  5. concentrationthe filtrate concentrated
  6. dissolutionThe residue is dissolved in 50 mL of EtOAc—2.5% aq. NaHCO3 (1:1)
  7. customthe layers separated
  8. extractionthe aqueous phase extracted with more ethyl acetate
  9. washThe combined organic layers are washed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe resulting crude product is purified by column chromatography (0–2% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-36f2971038d8417e92e0a9a291c80238
Source dataset
uspto-grants-2006_09
Patent number
US07101874B2

Reaction notes

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