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Triethyl phosphite → (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylic acid sodium salt

HRID 1081947
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1081947
C(=O)([O-])O.[Na+:5].CC1(C)CC(=O)CC(=O)C1.P(OCC)(OCC)OCC.C([O:29][C:30]([C:32]1[N:36]2[C:37](=[O:42])[C@H:38]([C@H:39]([OH:41])[CH3:40])[C@H:35]2[C@@H:34]([CH3:43])[C:33]=1[S:44][C@H:45]1[CH2:49][NH:48][C:47](=[S:50])[CH2:46]1)=[O:31])C=C>O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(O)C>[Na+:5].[NH:48]1[CH2:49][C@H:45]([S:44][C:33]2[C@H:34]([CH3:43])[C@@H:35]3[C@@H:38]([C@H:39]([OH:41])[CH3:40])[C:37](=[O:42])[N:36]3[C:32]=2[C:30]([O-:31])=[O:29])[CH2:46][C:47]1=[S:50]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 31215Triethyl phosphiteHCID 31358DimedoneHCID 516892Sodium BicarbonateHCID 10571982HCID 10571982, Verbindung

Produkt 1

HCID 23689827(1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylic acid sodium saltAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 167845palladium(II) acetateKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of sodium hydrogen carbonate (84 mg) in water (1 ml) is added dimedone (84 mg), and the mixture is dissolved by treating with ultrasonics. Thereto is added ethanol (8 ml), and further treated with ultrasonics for five minutes. To the mixture are added palladium diacetate (11 mg), triethyl phosphite (0.06 ml) and (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid allyl ester (383 mg) under nitrogen atmosphere, and the mixture is stirred at 35°-38° C. for one hour, and stirred at 20° C. for 10 minutes, and then stirred at 5° C. for 20 minutes. The precipitated crystals are collected by filtration to give (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt (157 mg). The mother liquor is concentrated under reduced pressure to remove the ethanol, and thereto is added water (20 ml). The mixture is washed five times with chloroform (20 ml), and the aqueous layer is subjected to lyophilization to give the above sodium salt (168 mg).

Aufarbeitung

  1. dissolutionthe mixture is dissolved
  2. additionby treating with ultrasonics
  3. additionfurther treated with ultrasonics for five minutes
  4. stirringstirred at 20° C. for 10 minutes
  5. stirringstirred at 5° C. for 20 minutes
  6. filtrationThe precipitated crystals are collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a825ad4ffdf040899b94f240c0162af5
Quelldatensatz
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05587474

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