Water → HCID 71252319, compound

HRID 2411418Notes

Reaction equation

HRID 2411418 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C@H:12]([CH2:13][OH:14])[CH2:11][CH2:10][S:9]2(=[O:16])=[O:15])[CH:5]=[C:4]([F:17])[C:3]=1[C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][N:27]=2)[CH2:22][CH2:21]1)=[O:19].[H-].[Na+].S(C1C=CC(C)=CC=1)(O[CH3:40])(=O)=O.O>O1CCCC1>[F:17][C:4]1[CH:5]=[C:6]([N:8]2[C@H:12]([CH2:13][O:14][CH3:40])[CH2:11][CH2:10][S:9]2(=[O:15])=[O:16])[CH:7]=[C:2]([F:1])[C:3]=1[C:18]([N:20]1[CH2:21][CH2:22][N:23]([C:26]2[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][N:27]=2)[CH2:24][CH2:25]1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 71251988HCID 71251988, compound

Product 1

HCID 71252319HCID 71252319, compoundYield 1.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-[2,6-difluoro-4-(3-hydroxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl][4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (270 mg) described in Example 35 was dissolved in tetrahydrofuran, sodium hydride (48 mg) was added, and the mixture was stirred at room temperature for 30 min. Then, to the reaction mixture was added methyl tosylate (203 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (5 mg).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-849b4cc562b94866be03d92bc8633f7f
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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