Acetone → HCID 68359227, compound

HRID 339907Notes

Reaction equation

HRID 339907 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:13][CH:12]=1)(=[O:9])=[O:8].C([Li])CCC.[CH3:35][C:36]([CH3:38])=[O:37].FC(F)(F)C(O)=O>C1COCC1.CCCCCC>[OH:37][C:36]([CH3:38])([CH3:35])[CH:10]([C:11]1[CH:12]=[CH:13][C:14]([CH2:17][N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)=[CH:15][CH:16]=1)[S:7]([NH2:6])(=[O:8])=[O:9]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 68292717HCID 68292717, compoundHCID 178418339Butyllithium

Product 1

HCID 68359227HCID 68359227, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under inert gas, 0.410 g of N-(2,4-dimethoxybenzyl)-C-(4-morpholin-4-ylmethylphenyl)methanesulfonamide was initially charged in 5 ml of THF and then, at −78° C., 1.34 ml of a 1.6 N butyllithium solution in hexane were added dropwise. The reaction mixture was stirred for 5 minutes and then 0.29 ml of acetone was added dropwise. The mixture was stirred at constant temperature for 5 minutes, 0.22 ml of trifluoroacetic acid were added and the mixture was allowed to come to room temperature. The solvent was removed under reduced pressure. The residue was dissolved in 10 ml of dichloromethane, and 2 ml of trifluoroacetic acid were added. After stirring at room temperature for 16 h, 20 ml of 1M HCl were added and the aqueous phase was removed and concentrated. This gave the crude product with a molecular weight of 364.9 g/mol (C15H25N2O4S), which was used without further purification.

Workup

  1. stirringThe mixture was stirred at constant temperature for 5 minutes
  2. customto come to room temperature
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in 10 ml of dichloromethane
  5. addition2 ml of trifluoroacetic acid were added
  6. stirringAfter stirring at room temperature for 16 h
  7. addition20 ml of 1M HCl were added
  8. customthe aqueous phase was removed
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-fd943185cadc4d8aa0fbc63bb8467617
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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