반응 #44367

반응 방정식

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

용매

Water

반응 조건

후처리

1. 1
   세척washed with ethyl acetate
2. 2
   건조The organic extracts were dried (MgSO4)
3. 3
   기타evaporated in vacuo
4. 4
   기타The residue was purified by flash column chromatography
5. 5
   세척eluting 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
   농축concentrated in vacuo
10. 10
    workup.ADDITIONTrituration with a mixture of ether and isohexane
11. 11
    기타gave a solid, which
12. 12
    기타was further purified by reverse phase HPLC

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)

출처