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Dimethylformamide → (E)-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 1445501
ノート
印刷プレビュー

反応式

HRID 1445501 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([OH:20])=O)=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[N:22](C=O)C.[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[O:32]N>CCN(CC)CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[C:17](/[O:32][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][O:26]3)\[C:18]([NH2:22])=[O:20])=[CH:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 68524810(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]acrylic acid

生成物 1

HCID 86621707(E)-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-(tetrahydro-pyran-2-yloxy)-acrylamide

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

To a mixture of 3.16 g (E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid and 170 ml DMF are added 1.06 g HOBtxH2O and 7.02 g Et3N. This mixture is stirred for 70 min at ambient temperature. 3.99 g EDCxHCl are added and the reaction mixture is stirred for additional 45 min. 0.812 g O-(tetrahydro-2H-pyran-2-yl)-hydroxylamin are added and the reaction mixture is stirred overnight. The solvent is evaporated and the residue is partitioned between ethyl acetate and water. The organic phase is dried, evaporated and the crude product is purified by silica gel flash chromatography.

後処理

  1. addition3.99 g EDCxHCl are added
  2. stirringthe reaction mixture is stirred for additional 45 min
  3. stirringthe reaction mixture is stirred overnight
  4. customThe solvent is evaporated
  5. customthe residue is partitioned between ethyl acetate and water
  6. customThe organic phase is dried
  7. customevaporated
  8. customthe crude product is purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-3d3b5d0757364e749d4a9278cd5e760e
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07666868B2

反応ノート

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