Potassium Carbonate → HCID 86607503, compound

HRID 898861Notes

Reaction equation

HRID 898861 reaction equation
[CH3:1][C@@H:2]1[C@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@:3]1([NH:14][S:15]([C:18]1[S:19][C:20]([N:23]2[CH:27]=[C:26]([C:28]#[C:29][Si](C)(C)C)[CH:25]=[N:24]2)=[CH:21][CH:22]=1)(=[O:17])=[O:16])[C:11]([OH:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].S([O-])(O)(=O)=O.[K+]>CO>[C:28]([C:26]1[CH:25]=[N:24][N:23]([C:20]2[S:19][C:18]([S:15]([NH:14][C@:3]3([C:11]([OH:13])=[O:12])[C@@H:4]([C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=4)[C@H:2]3[CH3:1])(=[O:16])=[O:17])=[CH:22][CH:21]=2)[CH:27]=1)#[CH:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 516920Potassium bisulfateHCID 67524999HCID 67524999, compound

Product 1

HCID 86607503HCID 86607503, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1S,2R,3R)-2-methyl-3-phenyl-1-[5-(4-trimethylsilanylethynyl-pyrazol-1-yl)-thiophene-2-sulfonylamino]-cyclopropanecarboxylic acid (66 mg, 0.13 mmol) in methanol (1.0 mL) was added potassium carbonate (36 mg, 0.26 mmol) at room temperature. After stirring for 1 hour without any modification, to the mixture was added 5% aqueous potassium hydrogen sulfate solution (3.0 mL). The aqueous layer was extracted three times with ethyl acetate (2.0 mL). The organic layer was washed with water (3.0 mL) and saturated aqueous sodium chloride solution (3.0 mL), and dried over sodium sulfate. After filtration and evaporation of the residue, chloroform (1.0 mL) was added to the obtained residue to allow precipitation of crystals. After slurry-washing and filtration, the residue was dried under reduced pressure to give the title compound (54 mg, yield 98%) as a pale-yellow powder.

Workup

  1. extractionThe aqueous layer was extracted three times with ethyl acetate (2.0 mL)
  2. washThe organic layer was washed with water (3.0 mL) and saturated aqueous sodium chloride solution (3.0 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and evaporation of the residue, chloroform (1.0 mL)
  5. additionwas added to the obtained residue
  6. customprecipitation of crystals
  7. washAfter slurry-washing
  8. filtrationfiltration
  9. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-c9c3fc8fbd1c4536a9d1bab20258c2c0
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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