Réaction #44367

Équation de réaction

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

Solvants

Water

Conditions de réaction

Traitement

1. 1
   Lavagewashed with ethyl acetate
2. 2
   SéchageThe organic extracts were dried (MgSO4)
3. 3
   Autreevaporated in vacuo
4. 4
   AutreThe residue was purified by flash column chromatography
5. 5
   Lavageeluting 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
   Concentrationconcentrated in vacuo
10. 10
    workup.ADDITIONTrituration with a mixture of ether and isohexane
11. 11
    Autregave a solid, which
12. 12
    Autrewas further purified by reverse phase HPLC

Mode opératoire

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)

Source