Acetone → HCID 68291813, compound

HRID 339893Notes

Reaction equation

HRID 339893 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:4]=1[CH2:5][NH:6][S:7]([CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[CH3:11])(=[O:9])=[O:8].C([Li])CCC.[CH3:33][C:34]([CH3:36])=[O:35].FC(F)(F)C(O)=O>C1COCC1.CCCCCC>[CH3:1][O:2][C:3]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:4]=1[CH2:5][NH:6][S:7]([C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:20])([CH3:21])[CH3:19])=[CH:14][CH:13]=1)([C:34]([OH:35])([CH3:36])[CH3:33])[CH3:11])(=[O:9])=[O:8]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 86705331HCID 86705331, compoundHCID 178418339Butyllithium

Product 1

HCID 68291813HCID 68291813, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under inert gas, 1.01 g of N-[2,4-dimethoxybenzyl]-1-(4-tert-butylphenyl)ethanesulfonamide were initially charged in 20 ml of THF and then, at a temperature of −75° C., 3.23 ml of a 1.6 N butyllithium solution in hexane were added dropwise and the mixture was stirred for 10 minutes. After the addition of 1.16 ml of acetone, the reaction mixture was stirred at constant temperature for 10 minutes. Subsequently, 0.45 ml of trifluoroacetic acid was added and the reaction solution was allowed to come to room temperature. After concentration by rotary evaporation, the crude product was purified using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (484 mg) with a molecular weight of 449.6 g/mol (C24H35NO5S).

Workup

  1. stirringthe reaction mixture was stirred at constant temperature for 10 minutes
  2. customto come to room temperature
  3. concentrationAfter concentration
  4. customby rotary evaporation
  5. customthe crude product was purified
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-e71023b548c94528ae0840a5522a4486
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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