Potassium Carbonate → HCID 15542646, compound

HRID 379004Notes

Reaction equation

HRID 379004 reaction equation
C([O:4][CH2:5][CH:6]([CH3:49])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:39][C:19]3[N:20]([CH2:30][C:31]4[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=4[F:38])[CH:21]=[C:22]([C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[C:23](=[O:24])[C:18]=3[C:17]=2N(CC2C=CC=CC=2)C)=[CH:12][CH:11]=1)=[O:8])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:30]([N:20]([CH2:21][C:17]1[C:18]2[C:23](=[O:24])[C:22]([C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])=[CH:21][N:20]([CH2:30][C:31]3[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=3[F:38])[C:19]=2[S:39][C:16]=1[C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[CH:6]([CH3:49])[CH2:5][OH:4])=[CH:11][CH:12]=1)[CH3:19])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 21697260HCID 21697260, compound

Product 1

HCID 15542646HCID 15542646, compoundYield 141.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in Example 2 (1.40 g) was dissolved in methanol (100 ml), and then to the solution was added potassium carbonate (2.0 g, 15 mmol), followed by stirring at room temperature for 15 minutes. The reaction mixture was partitioned between ethyl acetate (200 ml) and distilled water (300 ml), and then the water layer was extracted with ethyl acetate (100 ml). The combined extracts were washed with saline, and dried (Na2SO4), the solvent was distilled off under reduced pressure. The obtained residue was chromatographed on silica gel and recrystallized from ether to yield white crystals (0.95 g, 72%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (200 ml)
  2. distillationdistilled water (300 ml)
  3. extractionthe water layer was extracted with ethyl acetate (100 ml)
  4. washThe combined extracts were washed with saline
  5. dry with materialdried (Na2SO4)
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was chromatographed on silica gel
  8. customrecrystallized from ether

Sources & evidence

ORD record
ord-6ae177eeedd1471e86381dbffc931d19
Source dataset
uspto-grants-2001_10
Patent number
US06297255B1

Reaction notes

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