Potassium Carbonate → HCID 23138833, compound

HRID 1171659Notes

Reaction equation

HRID 1171659 reaction equation
C([S:4][CH:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH2:7]/[C:6]/1=[CH:24]\[C:25]1[N:26]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:27]=[CH:28][CH:29]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH:14]1([C:12](=[O:13])[CH:11]([N:8]2[CH2:9][CH2:10][CH:5]([SH:4])/[C:6](=[CH:24]/[C:25]3[N:26]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:27]=[CH:28][CH:29]=3)/[CH2:7]2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23138884HCID 23138884, compound

Product 1

HCID 23138833HCID 23138833, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-{[1-(ethoxycarbonylmethyl)pyrrol-2-yl]methylidene}piperidine (1.41 g) in ethanol (30 ml) was added potassium carbonate (4.00 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. After filtration, water was added to the filtrate, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by a preparative HPLC (YMC-Pack ODS-A; YMC, mobile phase: 80% acetonitrile/water) to afford the title compound (0.49 g, yield: 38%) as a colourless amorphous solid.

Workup

  1. temperaturecooling
  2. filtrationAfter filtration, water
  3. additionwas added to the filtrate
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by a preparative HPLC (YMC-Pack ODS-A; YMC, mobile phase: 80% acetonitrile/water)

Sources & evidence

ORD record
ord-b2a6056a5cf84b3eab9d42b0cac5ec9b
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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