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Hydrochloric Acid → (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

HRID 1196197
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1196197
Cl[CH2:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH3:11])=[CH2:4].C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.Cl.C(OCC)(=O)C>CS(C)=O.O.[Cl-].[Na+].O.C(OCC)C>[OH:30][CH2:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH3:11])=[CH2:4]
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Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 15000239HCID 15000239, Verbindung

Produkt 1

HCID 15000240(3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 3283Diethyl EtherLösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of (3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone (100 g) in dimethylsulfoxide (800 ml) and water (200 ml) were added cuprous oxide (57.6 g) and p-toluenesulfonic acid (107 g), and the resultant mixture was stirred at 50° C. for 1.5 hours and then cooled down with ice-cooling. Brine (3 liters), 2N hydrochloric acid (1 liter), ethyl acetate (2 liters) and diethyl ether (2 liters) were poured into the reaction mixture, followed by stirring for 0.5 hour. The aqueous layer was extracted with a mixture of ethyl acetate (1 liter) and diethyl ether (1 liter). The combined extracts were washed successively with brine (2 liters), 5% sodium bicarbonate (2 liters) and brine (2 liters) and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone.

Aufarbeitung

  1. temperaturecooled down with ice-
  2. temperaturecooling
  3. extractionThe aqueous layer was extracted with a mixture of ethyl acetate (1 liter) and diethyl ether (1 liter)
  4. washThe combined extracts were washed successively with brine (2 liters), 5% sodium bicarbonate (2 liters) and brine (2 liters)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationFiltration and concentration of the filtrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-11bc3c4b136d473fb215a35ab973be28
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05112966

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