Acetone → HCID 68291290, compound

HRID 339855Notes

Reaction equation

HRID 339855 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][S:16]([NH:19]CC2C=CC(OC)=CC=2OC)(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([Li])C=CC=CC=1.[CH3:38][C:39]([CH3:41])=[O:40].FC(F)(F)C(O)=O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([S:16]([NH2:19])(=[O:17])=[O:18])[C:39]([OH:40])([CH3:41])[CH3:38])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 68291873HCID 68291873, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 68291290HCID 68291290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

Under inert gas, 3.10 g of C-(3-benzyloxyphenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide were initially charged in 60 ml of THF, and then, at a temperature of −75° C., 12.00 ml of a 1.8 N phenyllithium solution were added dropwise. The reaction mixture was allowed to come to 0° C. and stirred briefly, then cooled again to −75° C., and 3.80 ml of acetone were added dropwise. After stirring for 10 minutes, 3 ml of trifluoroacetic acid were added and the mixture was allowed to come to room temperature. After the removal of the solvent under reduced pressure, the residue was dissolved in 20 ml of dichloromethane and admixed with 5.00 ml of trifluoroacetic acid. After stirring at room temperature for 2.5 hours, the reaction solution was neutralized cautiously with 2 N aqueous sodium hydroxide solution and then stirred overnight. The precipitate formed was filtered off with suction, washed with dichloromethane and cold water, and coevaporated twice with toluene. The crude product was purified by means of normal phase chromatography using a Flashmaster with a dichloromethane/methanol gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (2.06 g) with a molecular weight of 335.4 g/mol (C17H21NO4S).

Workup

  1. customto come to 0° C.
  2. stirringAfter stirring for 10 minutes
  3. customto come to room temperature
  4. customAfter the removal of the solvent under reduced pressure
  5. dissolutionthe residue was dissolved in 20 ml of dichloromethane
  6. stirringAfter stirring at room temperature for 2.5 hours
  7. stirringstirred overnight
  8. customThe precipitate formed
  9. filtrationwas filtered off with suction
  10. washwashed with dichloromethane and cold water
  11. customThe crude product was purified by means of normal phase chromatography
  12. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-cc0b767a7be74915b736289c43cfa0c6
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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