Reaktion #44367

Reaktionsgleichung

product

1-[(3,5′-dichloro-2′-hydroxy[1,1′-biphenyl]-4-yl)carbonyl]-pyrrolidine

tert-butyl bromoacetate

potassium carbonate

DMF

→

title compound

[[3′,5-dichloro-4′-(1-pyrrolidinylcarbonyl)[1,1′-biphenyl]-2-yl]oxy]-acetic acid

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with ethyl acetate
2. 2
   TrocknenThe organic extracts were dried (MgSO4)
3. 3
   Sonstigeevaporated in vacuo
4. 4
   SonstigeThe residue was purified by flash column chromatography
5. 5
   Wascheneluting with isohexane:ethyl acetate (8:2)
6. 6
   workup.DISSOLUTIONThe sub-title compound was dissolved in DCM (8 ml)
7. 7
   workup.ADDITIONTFA (2 ml) was added
8. 8
   workup.STIRRINGstirred for 1 h
9. 9
   Einengenconcentrated in vacuo
10. 10
    workup.ADDITIONTrituration with a mixture of ether and isohexane
11. 11
    Sonstigegave a solid, which
12. 12
    Sonstigewas further purified by reverse phase HPLC

Vorschrift

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)

Quelle