Potassium Carbonate → HCID 131724879, compound

HRID 2181569Notes

Reaction equation

HRID 2181569 reaction equation
[ClH:1].[OH:2][NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:11][CH2:10][N:9](CC#C)[CH2:8][CH2:7]1)=[O:5].C([O-])([O-])=O.[K+].[K+].C1(S)CCCCC1>CN(C=O)C>[ClH:1].[CH:25]1([S:24][C:21]2[CH:20]=[CH:19][C:18]([S:15]([C:6]3([C:4]([NH:3][OH:2])=[O:5])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]3)(=[O:17])=[O:16])=[CH:23][CH:22]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15290CyclohexanethiolHCID 9890734HCID 9890734, compound

Product 1

HCID 131724879HCID 131724879, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part A: To a solution of the sulfone of Example 9, part D (10.1 g, 24.0 mmol) in DMF (20 mL) were added K2CO3 (5.0 g, 36.0 mmol) and cyclohexylmercaptan (4.4 mL, 36.0 mmol), and the solution was heated at 85 degrees Celsius for 6.5 hours. The solution was partitioned between ethyl acetate and H2O. The organic layer was washed with saturated NaCl and dried over magnesium sulfate. Chromatography (on silica, ethyl acetate/hexane) provided the sulfide as a oil (8.2 g, 67%).

Workup

  1. temperaturethe solution was heated at 85 degrees Celsius for 6.5 hours
  2. customThe solution was partitioned between ethyl acetate and H2O
  3. washThe organic layer was washed with saturated NaCl
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-fb04f6f9eefb4e159b69bf99d5cba177
Source dataset
uspto-grants-2005_05
Patent number
US06890937B2

Reaction notes

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