反応 #44367

反応方程式

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

溶媒

Water

反応条件

後処理

1. 1
   洗浄washed with ethyl acetate
2. 2
   乾燥The organic extracts were dried (MgSO4)
3. 3
   その他evaporated in vacuo
4. 4
   その他The residue was purified by flash column chromatography
5. 5
   洗浄eluting 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
   濃縮concentrated in vacuo
10. 10
    workup.ADDITIONTrituration with a mixture of ether and isohexane
11. 11
    その他gave a solid, which
12. 12
    その他was further purified by reverse phase HPLC

実験手順

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)

出典