Cesium carbonate → (2-{2-[(2R)-2-carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic Acid tert-butyl Ester

HRID 11707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11707
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][C@H:11]2[CH2:24][C:25]([NH2:27])=[O:26])=[O:9])=[C:4]([OH:30])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]>O1CCOCC1>[C:42]([O:41][C:39](=[O:40])[CH2:38][O:30][C:4]1[CH:3]=[C:2]([Cl:1])[CH:29]=[CH:28][C:5]=1[O:6][CH2:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][C@H:11]1[CH2:24][C:25](=[O:26])[NH2:27])=[O:9])([CH3:45])([CH3:44])[CH3:43]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 69655726(2R)-2-[1-[(4-Chloro-2-hydroxy-phenoxy)-acetyl]-4-(4-fluoro-benzyl)-piperazin-2-yl]-acetamide

Produkt 1

HCID 69656159(2-{2-[(2R)-2-carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic Acid tert-butyl EsterAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(2R)-2-[1-[(4-Chloro-2-hydroxy-phenoxy)-acetyl]-4-(4-fluoro-benzyl)-piperazin-2-yl]-acetamide (0.070 g, 0.16 mmol), cesium carbonate (0.078 g, 0.24 mmol) and tert-butyl bromoacetate (0.038 g, 0.028 mL, 0.193 mmol) were stirred in dioxane (2 mL). After 2.5 days, the solution was filtered, concentrated and chromatographed on silica gel to yield the title compound as a white solid (0.077 g).

Aufarbeitung

  1. filtrationthe solution was filtered
  2. concentrationconcentrated
  3. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-cf0e8160df2f4b5284c3b3935cb1a9cb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

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