Water → HCID 21098767, compound

HRID 1351982Notes

Reaction equation

HRID 1351982 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH3:15])[CH:5]([OH:14])[C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>O1CCCC1>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:14][CH:5]([C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[O:7])[CH:4]([CH3:15])[CH3:3])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 22340959HCID 22340959, compound

Product 1

HCID 21098767HCID 21098767, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under ice-cooling, to a solution of 60% sodium hydride (136 mg, 3.41 mmol) in tetrahydrofuran (5 mL) is added dropwise a solution of 3-methyl-1-morpholin-4-yl-1-oxobutan-2-ol (426 mg, 2.27 mmol) in tetrahydrofuran (15 mL), and the mixture is stirred at room temperature for 2 hours. To the reaction solution is added p-toluene-sulfonyl chloride (651 mg, 3.42 mmol), and the mixture is stirred at room temperature for 2 hours. After the reaction is completed, water is added to the mixture, and the mixture is extracted with ethyl acetate. This organic layer is washed with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated brine, and dried over anhydrous magnesium sulfate. The solvent is removed by distillation, and the obtained residue is purified by silica gel column chromatography (chloroform) to give the title compound (701 mg, yield: 90%).

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThis organic layer is washed with water
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent is removed by distillation
  6. customthe obtained residue is purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-2e8b61740dc347718767881ecf56035b
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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