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Methyl iodide → HCID 67200495, Verbindung

HRID 551705
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 551705
[H-].[Na+].O1CCC[CH2:4]1.[C:8]([O:12][C:13]([NH:15][CH2:16][C@@:17]1([CH2:26][C:27]([OH:29])=[O:28])[CH2:23][C@H:22]2[C@@H:18]1[CH:19]=[C:20]([CH2:24][CH3:25])[CH2:21]2)=[O:14])([CH3:11])([CH3:10])[CH3:9].CI>O>[C:8]([O:12][C:13]([N:15]([CH2:16][C@@:17]1([CH2:26][C:27]([OH:29])=[O:28])[CH2:23][C@H:22]2[C@@H:18]1[CH:19]=[C:20]([CH2:24][CH3:25])[CH2:21]2)[CH3:4])=[O:14])([CH3:9])([CH3:10])[CH3:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 67197694[(1S,5R,6R)-6-{[(tert-butoxycarbonyl)amino]methyl}-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetic acid

Produkt 1

HCID 67200495HCID 67200495, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

Sodium hydride (63%, 2.48 g, 65.0 mmol) was added in small portions to a tetrahydrofuran solution (25 mL) of [(1S,5R,6R)-6-{[(tert-butoxycarbonyl)amino]methyl}-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetic acid (2.01 g, 6.50 mmol) and methyl iodide (4.05 mL, 65.0 mmol) with stirring at room temperature. The mixture was stirred at this temperature for 6 hours, and water (50 mL) was then added thereto while the reaction solution was cooled on ice, followed by washing with diethyl ether. The aqueous layer was made acidic using 1 M citric acid, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (2.00 g, 95%).

Aufarbeitung

  1. stirringThe mixture was stirred at this temperature for 6 hours
  2. temperaturewhile the reaction solution was cooled on ice
  3. washby washing with diethyl ether
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationThe residue was filtered
  7. concentrationconcentrated under reduced pressure
  8. customThen, the obtained crude product
  9. customwas purified by silica gel column chromatography
  10. customto obtain the compound of interest as an oil substance (2.00 g, 95%)

Quellen und Nachweise

ORD-Eintrag
ord-a4e685df95384412af667ddd03e0ad42
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07947738B2

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