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

HRID 1023781
Notes
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Reaction equation

HRID 1023781 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-1591ec44d9b34c9b9163e3ba3429d018
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722741B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes