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

HRID 1695135
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HRID 1695135 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 67277611HCID 67277611, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water
용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-c9d9196e2a1742038642391c4f7fb817
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163727B2

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