Cesium carbonate → methyl 4-((4-acetoxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)benzoate

HRID 1686254Notes

Reaction equation

HRID 1686254 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](=[O:23])(=[O:22])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:31][C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1>CC(C)=O>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:12]([CH2:31][C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])(=[O:23])=[O:22])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 574223444-(N-(2-methoxybenzyl)sulfamoyl)phenyl acetate

Product 1

HCID 66974740methyl 4-((4-acetoxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(N-(2-methoxybenzyl)sulfamoyl)phenyl acetate (example 5-42a) (50 mg, 0.15 mmol) was dissolved in acetone (1.0 mL) followed by the addition of cesium carbonate (97 mg, 0.30 mmol) and methyl 4-(bromomethyl)benzoate (38 mg, 0.17 mmol). The mixture was stirred at room temperature overnight and then the inorganic salts were filtered off. Acetone was removed in vacuo and the residue was re-dissolved in ethyl acetate and washed with water followed by brine. The organic layer was dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography with ethyl acetate/hexanes as the eluent to afford methyl 4-((4-acetoxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)benzoate.

Workup

  1. filtrationthe inorganic salts were filtered off
  2. customAcetone was removed in vacuo
  3. dissolutionthe residue was re-dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography with ethyl acetate/hexanes as the eluent

Sources & evidence

ORD record
ord-a05ffba02b6d4be5b8bcde2d797c2399
Source dataset
uspto-grants-2012_04
Patent number
US08148544B2

Reaction notes

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