Acetone → 2-(4-Bromophenyl)-3-hydroxy-3-methylbutane-2-sulfonamide

HRID 339886Notes

Reaction equation

HRID 339886 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH:10]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)[CH3:11])(=[O:9])=[O:8].C[Li].[CH3:27]C(C)=O.F[C:32](F)(F)[C:33]([OH:35])=O>C1COCC1.C(OCC)C>[Br:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]([S:7]([NH2:6])(=[O:8])=[O:9])([C:33]([OH:35])([CH3:32])[CH3:27])[CH3:11])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 86705325N-(2,4-dimethoxybenzyl)-1-(4-bromophenyl)ethanesulfonamideHCID 178418348HCID 178418348, compound

Product 1

HCID 682917312-(4-Bromophenyl)-3-hydroxy-3-methylbutane-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under inert gas, 2.58 g of N-(2,4-dimethoxybenzyl)-1-(4-bromophenyl)ethanesulfonamide was initially charged in 40 ml of THF, and then, at a temperature of −78° C., 7.90 ml of a 1.6 N methyllithium solution in diethyl ether were added dropwise and the mixture was stirred at constant temperature for 10 minutes. Subsequently, 2.47 ml of acetone were added. After stirring for 15 minutes, the reaction solution was admixed with 0.96 ml of trifluoroacetic acid and allowed to warm up to room temperature. After the removal of the solvent under reduced pressure, the residue was dissolved in 50 ml of dichloromethane, 10 ml of trifluoroacetic acid were added and the mixture was stirred at room temperature for 1 hour. 100 ml of methanol were added to the reaction solution and the solvent was concentrated by rotary evaporation. The crude product was purified by filtration through a silica gel column. The column was washed through with ethyl acetate until no further product eluted. The eluate was concentrated by rotary evaporation and the residue (2.01 g) was used in the next reaction without further purification.

Workup

  1. stirringAfter stirring for 15 minutes
  2. customAfter the removal of the solvent under reduced pressure
  3. dissolutionthe residue was dissolved in 50 ml of dichloromethane
  4. addition10 ml of trifluoroacetic acid were added
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. addition100 ml of methanol were added to the reaction solution
  7. concentrationthe solvent was concentrated by rotary evaporation
  8. filtrationThe crude product was purified by filtration through a silica gel column
  9. washThe column was washed through with ethyl acetate until no further product
  10. washeluted
  11. concentrationThe eluate was concentrated by rotary evaporation
  12. customthe residue (2.01 g) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-ea6ccae0515b40f381ca01a527a24450
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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