Hydrochloric Acid → (S)-[4-(2,4-dimethylphenyl)piperazin-1-yl][4-(3-hydroxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanone

HRID 2411414Notes

Reaction equation

HRID 2411414 reaction equation
C([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[N:11]1[C:17]1[CH:22]=[CH:21][C:20]([C:23]([N:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:32]=3[CH3:38])[CH2:27][CH2:26]2)=[O:24])=[C:19]([S:39]([CH3:42])(=[O:41])=[O:40])[CH:18]=1)C1C=CC=CC=1.Cl>C(O)C.[C].[Pd]>[CH3:38][C:32]1[CH:33]=[C:34]([CH3:37])[CH:35]=[CH:36][C:31]=1[N:28]1[CH2:29][CH2:30][N:25]([C:23]([C:20]2[CH:21]=[CH:22][C:17]([N:11]3[C@H:10]([CH2:9][OH:8])[CH2:14][CH2:13][S:12]3(=[O:15])=[O:16])=[CH:18][C:19]=2[S:39]([CH3:42])(=[O:40])=[O:41])=[O:24])[CH2:26][CH2:27]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71252629(S)-[4-(3-benzyloxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

Product 1

HCID 71251962(S)-[4-(2,4-dimethylphenyl)piperazin-1-yl][4-(3-hydroxymethyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)-2-methanesulfonylphenyl]methanoneYield 88.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(S)-[4-(3-benzyloxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methanesulfonylphenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (930 mg) described in Example 27 was dissolved in ethanol (50 mL), palladium carbon (200 mg) and 1N hydrochloric acid (2 mL) were added, and the mixture was stirred at room temperature for 3.5 hr under a hydrogen atmosphere. The insoluble material was separated by filtration from the reaction mixture, and the filtrate was concentrated. To the obtained residue was added 1N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (705 mg).

Workup

  1. customThe insoluble material was separated by filtration from the reaction mixture
  2. concentrationthe filtrate was concentrated
  3. additionTo the obtained residue was added 1N aqueous sodium hydroxide solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-b167120fdd054133b1d5e4c080f632e8
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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