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Sodium Sulfide → HCID 10989032, Verbindung

HRID 1268709
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1268709
[CH3:1][C:2]1([CH3:26])[O:6][C@@H:5]([C@H:7](OS(C)(=O)=O)[C@@H:8]2[C@H:12]([CH2:13]OS(C)(=O)=O)[O:11][C:10]([CH3:20])([CH3:19])[O:9]2)[CH2:4][O:3]1.[S-2:27].[Na+].[Na+]>CN(C)C=O>[CH3:1][C:2]1([CH3:26])[O:6][C@@H:5]([C@@H:7]2[C@@H:8]3[C@@H:12]([O:11][C:10]([CH3:20])([CH3:19])[O:9]3)[CH2:13][S:27]2)[CH2:4][O:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14804Sodium SulfideHCID 11026162Methanesulfonic acid (4S,5S)-5-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-YL)-methanesulfonyloxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Produkt 1

HCID 10989032HCID 10989032, VerbindungAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

10.1 g (0.024 mol) of methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester from the aforementioned Experimental Example 3 were dissolved in 260 mL of N,N-dimethylformamide, and 8.9 g (0.036 mol) of sodium sulfide were added. The reaction mixture was reacted at 100° C. for 3 h. The reaction mixture was concentrated under reduced pressure, and water was added to the concentrate, which was then extracted with ethyl acetate. The organic layer was dried and filtered, and the filtrate was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography using the eluant (hexane:ethyl acetate=5:1) to obtain 5.9 g (yield: 94%) of (3aS,4R,6aR)-4-((4R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole as an oil.

Aufarbeitung

  1. customThe reaction mixture was reacted at 100° C. for 3 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  3. additionwas added to the concentrate, which
  4. extractionwas then extracted with ethyl acetate
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe concentrate was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8c40118bbd73436f8c5b17b297465629
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07199127B2

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