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Methanol → (3S,4S)-4-methoxycarbonyl-3-(1-(R)-hydroxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

HRID 1196209
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1196209
[C:1]([C@H:4]1[N:7]([CH:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:6](=[O:27])[C@@H:5]1[C@H:28]([OH:30])[CH3:29])([OH:3])=[O:2].S(=O)(=O)(O)O.[OH-].[Na+].[CH3:38]O>>[CH3:38][O:2][C:1]([C@H:4]1[N:7]([CH:8]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[C:6](=[O:27])[C@@H:5]1[C@H:28]([OH:30])[CH3:29])=[O:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67798242HCID 67798242, Verbindung

Produkt 1

HCID 14050669(3S,4S)-4-methoxycarbonyl-3-(1-(R)-hydroxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of (3S,4S)-4-carboxy-3-(1-(R)-hydroxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (34 g) in methanol (310 ml) was added 98% sulfuric acid (2.9 g), and the resultant mixture was heated at 65° C. for 3 hours, cooled down to 40° C., neutralized with 8% sodium hydroxide (15 ml) and concentrated to make a one third volume. The concentrate was diluted with 1,2-dichloroethane (105 ml) and washed with water. The aqueous layer was separated from the organic layer and extracted with 1,2-dichloroethane (105 ml). The extracts and the organic layer were combined together, washed with water and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave (3S,4S)-4-methoxycarbonyl-3-(1-(R)-hydroxyethyl)-1-di(p-anisyl)methyl-2-azetidinone. m.p., 102°-104° C.

Aufarbeitung

  1. concentrationconcentrated
  2. additionThe concentrate was diluted with 1,2-dichloroethane (105 ml)
  3. washwashed with water
  4. customThe aqueous layer was separated from the organic layer
  5. extractionextracted with 1,2-dichloroethane (105 ml)
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationFiltration and concentration of the filtrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cd63a47de8d9484688958515fe8d1364
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05112966

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