Cesium carbonate → Ethyl 2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetate

HRID 2209707Notes

Reaction equation

HRID 2209707 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C)C=O>[CH2:29]([O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:18][CH:19]([CH3:20])[CH3:21])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 125271-IodohexaneHCID 10591435Ethyl 2-[[4-hydroxybenzenesulfonyl](isobutyl)amino]acetate

Product 1

HCID 10834775Ethyl 2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-[[4-hydroxybenzenesulfonyl](isobutyl)amino]acetate (1.0 g, 3.17 mmol) is dissolved in dimethylformamide (16 mL). Cesium carbonate (1.03 g, 3.17 mmol) is added, followed by 1-iodohexane (0.47 mL, 3.17 mmol), and the reaction is stirred overnight at room temperature. The reaction is then partitioned between water and ethyl acetate, the aqueous layer is extracted well with ethyl acetate, the combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (10% ethyl acetate/hexane) to give ethyl 2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetate.

Workup

  1. customThe reaction is then partitioned between water and ethyl acetate
  2. extractionthe aqueous layer is extracted well with ethyl acetate
  3. dry with materialthe combined organic layers are dried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe product is purified by silica gel chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-617717109e5b4dd7947342cfe24ccecc
Source dataset
uspto-grants-1995_10
Patent number
US05455258

Reaction notes

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