Methyl iodide → (S)-2-ethoxy-3-[4-{2-(4-[methylsulfonyl(methyl)amino]phenyl)ethoxy}phenyl]propanoic acid ethyl ester

HRID 987309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987309
[CH2:1]([O:3][C:4](=[O:30])[C@@H:5]([O:27][CH2:28][CH3:29])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)[CH3:2].I[CH3:32].[H-].[Na+]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:30])[C@@H:5]([O:27][CH2:28][CH3:29])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]([S:23]([CH3:26])(=[O:25])=[O:24])[CH3:32])=[CH:18][CH:17]=2)=[CH:11][CH:12]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54054668(S)-2-ethoxy-3-[4-{2-(4-[methylsulfonylamino]phenyl)ethoxy}phenyl]propanoic acid ethyl ester

Produkt 1

HCID 53881407(S)-2-ethoxy-3-[4-{2-(4-[methylsulfonyl(methyl)amino]phenyl)ethoxy}phenyl]propanoic acid ethyl esterAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(S)-2-Ethoxy-3-[4-{2-(4-[methylsulfonylamino]phenyl)ethoxy}phenyl]propanoic acid ethyl ester (0.17 g; 0.39 mmole) was dissolved in tetrahydrofuran (10 ml). Iodomethane (0.277 g; 1.95 mmole) and sodium hydride (0.019 g; 0.79 mmole) were added and the reaction mixture was stirred at room temperature for 3 hours and then evaporated. The residue was redissolved and extracted with diethyl ether and water. The organic phase was washed once more with water, dried with sodium sulfate and evaporated. Chromatography with ethyl acetate:petroleum ether (1:1) gave 0.098 g (55.8% yield) of (S)-2-ethoxy-3-[4-{2-(4-[methylsulfonyl(methyl)amino]phenyl)ethoxy}phenyl]propanoic acid ethyl ester.

Aufarbeitung

  1. customevaporated
  2. dissolutionThe residue was redissolved
  3. extractionextracted with diethyl ether and water
  4. washThe organic phase was washed once more with water
  5. dry with materialdried with sodium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1b2dda1d7efa4a8f812bdd9ec70445d0
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630600B1

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