4-Hydroxybiphenyl → (2S)-3-{4-[2-(biphenyl-4-yloxy)-ethoxy]-phenyl}-2-methoxy-propionic acid

HRID 459301

Reaktionsgleichung

Reaktionsgleichung von HRID 459301
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][C:4]([OH:7])=[CH:3][CH:2]=1.C([O:16][C:17](=[O:32])[C@@H:18]([O:30][CH3:31])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28]Br)=[CH:22][CH:21]=1)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:2]=[CH:3][C:4]([O:7][CH2:28][CH2:27][O:26][C:23]2[CH:22]=[CH:21][C:20]([CH2:19][C@H:18]([O:30][CH3:31])[C:17]([OH:32])=[O:16])=[CH:25][CH:24]=2)=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 71034-HydroxybiphenylHCID 10796Cesium carbonateHCID 58822865(2S)-3-[4-(2-bromo-ethoxy)-phenyl]2-methoxy-propionic acid ethyl ester

Produkt 1

HCID 10135109(2S)-3-{4-[2-(biphenyl-4-yloxy)-ethoxy]-phenyl}-2-methoxy-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of biphenyl-4-ol (0.39 mmol, 68 mg) in 10 ml of DMF in was treated with (2S)-3-[4-(2-bromo-ethoxy)-phenyl]-2-methoxy-propionic acid ethyl ester obtained in Step 2 (0.33 mmol, 100 mg) and cesium carbonate (0.66 mmol, 214 mg) in a round bottom flask. The reactants were filtered and was washed with DMF several times and the solvent was evaporated under vacuo. The residue was reconstituted in a mixture of ethanol (20 ml) and NaOH (1M) (8 ml), and then stirred at room temperature until TLC indicated the disappearance of starting material. Ethanol was removed under vacuum, and the aqueous solution was diluted with 20 ml of brine and washed with diethyl ether (3×15 mL). The aqueous phase was acidified with

Aufarbeitung

  1. filtrationThe reactants were filtered
  2. washwas washed with DMF several times
  3. customthe solvent was evaporated under vacuo
  4. additionThe residue was reconstituted in a mixture of ethanol (20 ml) and NaOH (1M) (8 ml)
  5. customEthanol was removed under vacuum
  6. additionthe aqueous solution was diluted with 20 ml of brine
  7. washwashed with diethyl ether (3×15 mL)

Quellen und Nachweise

ORD-Eintrag
ord-ea7eb437cf5f4e2d980a993b393603bb
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192982B2

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