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

HRID 865533노트

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HRID 865533 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a9cb1f85da3c422693695c3ec5da99eb
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565485

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