Water → Benzyl 4-sulfamoylbutanoate

HRID 1186447Notes

Reaction equation

HRID 1186447 reaction equation
[S:1]([CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])(=[O:4])(=[O:3])[NH2:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C>[S:1]([CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:9])(=[O:4])(=[O:3])[NH2:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 27733204-sulfamoylbutanoic Acid

Product 1

HCID 66674779Benzyl 4-sulfamoylbutanoateYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Sulfamoylbutanoic acid (1.00 g, 5.98 mmol) was dissolved in DMF (6.00 mL). To this, cesium carbonate (994 mg, 3.05 mmol) and benzyl bromide (0.711 mL, 5.98 mmol) were added and the mixture was stirred at room temperature for 18 hours. The reaction was stopped by addition of water, and the organic layer was extracted with dichloromethane, washed with a saturated aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was subjected to slurry purification using diethyl ether, to give Compound GM (940 mg, yield: 61%).

Workup

  1. extractionthe organic layer was extracted with dichloromethane
  2. washwashed with a saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. custompurification
  6. customto give Compound GM (940 mg, yield: 61%)

Sources & evidence

ORD record
ord-c3380aed1a194fbea185964e991ff018
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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