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

HRID 1033460
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1033460
[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), there was added 98% sulfuric acid (2.9 g). The resultant mixture was heated at 65° C. for 3 hours, cooled down to 40° C., neutralized with 8% aqueous sodium hydroxide solution (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 extract was combined with the organic layer, washed with water and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo to give (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. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f50601e1641c419dad49cd2b7c10b50e
Quelldatensatz
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05310897

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