Cesium carbonate → HCID 68869796, Verbindung

HRID 1985253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1985253
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([O:14][CH3:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:17][N:18]1[CH:22]([CH2:23][CH2:24]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:21][N:20]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=2)[C:19]1=[O:47].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([O:14][CH3:15])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:24][CH2:23][CH:22]2[CH2:21][N:20]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:45])([F:46])[F:44])=[CH:39][CH:38]=3)[C:19](=[O:47])[N:18]2[CH3:17])=[CH:11][CH:12]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 18794793Ethyl 3-(4-hydroxyphenyl)-2-methoxypropanoateHCID 86596229HCID 86596229, Verbindung

Produkt 1

HCID 68869796HCID 68869796, VerbindungAusbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 3-(4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl ester 0.027 g, 0.120 mmol), toluene-4-sulfonic acid 2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethyl ester (0.061 g, 0.133 mmol) and Cs2CO3 (0.059 g, 0.181 mmol) in DMF (4 mL) was heated to 55° C. under N2 for 16 h. The reaction was cooled and quenched with 1 N HCl (10 mL) and worked up extractively with Et2O and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using 4:1 then 3:1 hexanes:acetone to afford 0.040 g (64%) 2-methoxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid ethyl ester. 1H NMR. MS (ES+) Calc'd for C26H32N2O5F3 (M+1) 509. Found m/z 509 (100%).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customquenched with 1 N HCl (10 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto afford crude product that
  6. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ef55995f30034dd3b77b9284716ef2ce
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544812B2

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