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Dimethylformamide → [[3',5-Dichloro-4'-(1-pyrrolidinylcarbonyl)[1,1'-biphenyl]-2-yl]oxy]-acetic acid

HRID 16089
ノート
印刷プレビュー

反応式

HRID 16089 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[OH:22])[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9].Br[CH2:24][C:25]([O:27]C(C)(C)C)=[O:26].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH2:24][C:25]([OH:27])=[O:26])[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 67277611HCID 67277611、化合物

生成物 1

HCID 11538448[[3',5-Dichloro-4'-(1-pyrrolidinylcarbonyl)[1,1'-biphenyl]-2-yl]oxy]-acetic acid

試薬・触媒・溶媒 1

HCID 962Water
溶媒

実験手順

The product from step c) (180 mg), tert-butyl bromoacetate (0.07 ml), potassium carbonate (0.1 g) and DMF (10 ml) were charged to a flask and stirred for 16 h. Water was added and then washed with ethyl acetate. The organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography eluting with isohexane:ethyl acetate (8:2). The sub-title compound was dissolved in DCM (8 ml) and TFA (2 ml) was added, stirred for 1 h, then concentrated in vacuo. Trituration with a mixture of ether and isohexane gave a solid, which was further purified by reverse phase HPLC to give the title compound. Yield (48 mg)

後処理

  1. washwashed with ethyl acetate
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by flash column chromatography
  5. washeluting with isohexane:ethyl acetate (8:2)
  6. dissolutionThe sub-title compound was dissolved in DCM (8 ml)
  7. additionTFA (2 ml) was added
  8. stirringstirred for 1 h
  9. concentrationconcentrated in vacuo
  10. additionTrituration with a mixture of ether and isohexane
  11. customgave a solid, which
  12. customwas further purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-77362c6764ac4e2fb0ace2edf1e7fcf2
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737135B2

反応ノート

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