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

HRID 1378859ノート

反応式

HRID 1378859 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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, saturated 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.

後処理

  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, saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was dried in vacuo

出典と根拠

ORDレコード
ord-060a0cc44d0f403d8209a58065367fa4
出典データセット
uspto-grants-1997_09
特許番号
US05668176

反応ノート

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