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Dimethylamine → HCID 57210056, Verbindung

HRID 1976365
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1976365
[CH3:1][NH:2][CH3:3].ClCCl.[CH3:7][O:8][C:9]([C:11]1[C@H:12]2[CH2:29][C@@H:28]3[O:30][C@:27]3(C)[C@@H:13]2[C@H:14]([O:17][C:18](OC2C=CC=CC=2)=[O:19])[O:15][CH:16]=1)=[O:10]>CCCCCC.C(OCC)(=O)C>[CH3:7][O:8][C:9]([C:11]1[C@H:12]2[CH2:29][C@@H:28]3[O:30][C@@H:27]3[C@@H:13]2[C@H:14]([O:17][C:18](=[O:19])[N:2]([CH3:3])[CH3:1])[O:15][CH:16]=1)=[O:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 6344DichloromethaneHCID 57009109HCID 57009109, Verbindung

Produkt 1

HCID 57210056HCID 57210056, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

5 ml of a 50% aqueous dimethylamine solution were added to a dichloromethane solution containing 198 mg of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(phenoxycarbonyloxy) cyclopenta [c] pyrane-4-carboxylic acid methylester described in Example 10 followed by stirring for 10 minutes at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with brine, it was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless powder from the hexane-ethyl acetate eluate in the form of (1S,4aS,6S,7R,7aR)-1-(dimethylcarbamoyloxy)-6,7-epoxy-1,4a,5,6,7,7a-hexahydrocyclopenta [c] pyrane-4-carboxylic acid methylester (140 mg, yield: 83%). The physicochemical properties of this compound are described in Table 7. Compound No. 31.

Aufarbeitung

  1. extractionThe reaction mixture was then extracted with dichloromethane
  2. washAfter washing the organic phase with brine, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b0b2f7ad60f14f5289444ed1724a734e
Quelldatensatz
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06225478B1

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