Cesium carbonate → Methyl alpha-(2-n-propyl-4-aminosulfonyl-phenoxy)-3,4-methylenedioxyphenylacetate

HRID 865533Notes

Reaction equation

HRID 865533 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:22]([C:27]1[CH:32]=[CH:31][C:30]2[O:33][CH2:34][O:35][C:29]=2[CH:28]=1)[C:23]([O:25][CH3:26])=[O:24]>CN(C=O)C>[CH2:12]([C:3]1[CH:4]=[C:5]([S:8]([NH2:11])(=[O:9])=[O:10])[CH:6]=[CH:7][C:2]=1[O:1][CH:22]([C:27]1[CH:32]=[CH:31][C:30]2[O:33][CH2:34][O:35][C:29]=2[CH:28]=1)[C:23]([O:25][CH3:26])=[O:24])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11821769Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetateHCID 190804514-Hydroxy-3-n-propylbenzenesulfonamide

Product 1

HCID 19080400Methyl alpha-(2-n-propyl-4-aminosulfonyl-phenoxy)-3,4-methylenedioxyphenylacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.06 g (14.23 mmol) of the product of Step B dissolved in 25 mL of anhydrous DMF was added 4.87 g (15.0 mmol) of cesium carbonate and the reaction mixture was magnetically stirred under a nitrogen atmosphere at room temperature for 15 minutes. Methyl α-bromo-3,4-methylenedioxyphenylacetate (4.08 g, 15.0 mmol) was then added and the reaction mixture was stirred for an additional 3 hours. The reaction mixture was then partitioned between EtOAc (80 mL) and 10% aqueous citric acid (300 mL). The organic layer was separated, washed with saturated aqueous NaHCO3, satuarated aqueous NaCl, dried (MgSO4), filtered and evaporated. The residue was dried in vacuo to afford 5.90 g (5.79 theoretical) of the title compound which was used in the next step without further purification.

Workup

  1. stirringthe reaction mixture was stirred for an additional 3 hours
  2. customThe reaction mixture was then partitioned between EtOAc (80 mL) and 10% aqueous citric acid (300 mL)
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-a9cb1f85da3c422693695c3ec5da99eb
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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