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

HRID 1081948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081948
CC1(C)CC(=O)CC(=O)C1.O1CCOCC1.P(OCC)(OCC)OCC.C([O:30][C:31]([C:33]1[N:37]2[C:38](=[O:50])[C@H:39]([C@H:40]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[CH3:41])[C@H:36]2[C@@H:35]([CH3:51])[C:34]=1[S:52][C@H:53]1[CH2:57][NH:56][C:55](=[S:58])[CH2:54]1)=[O:32])C=C.C(=O)([O-])O.[Na+:63]>O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(OCC)C>[Na+:63].[NH:56]1[CH2:57][C@H:53]([S:52][C:34]2[C@H:35]([CH3:51])[C@@H:36]3[C@@H:39]([C@H:40]([O:42][Si:43]([C:46]([CH3:48])([CH3:47])[CH3:49])([CH3:44])[CH3:45])[CH3:41])[C:38](=[O:50])[N:37]3[C:33]=2[C:31]([O-:32])=[O:30])[CH2:54][C:55]1=[S:58]

Komponenten

9

Edukt 5

HCID 31215Triethyl phosphiteHCID 312751,4-DioxaneHCID 31358DimedoneHCID 516892Sodium BicarbonateHCID 10720094HCID 10720094, Verbindung

Produkt 1

HCID 23709518(1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium saltAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

Dimedone (169 mg) is dissolved in a solution of sodium hydrogen carbonate (169 mg) in water (2 ml) by ultrasonic treatment, and thereto are added dioxane (16 ml), palladium diacetate (23 mg) and triethyl phosphite (0.12 ml) under nitrogen atmosphere, and further added thereto (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid allyl ester (1.03 g). The mixture is stirred at 30° C. for 30 minutes, and thereto is added diethyl ether (32 ml), and the mixture is stirred at 25° C. for 15 minutes, and further stirred at 5° C. for 30 minutes. The precipitated crystals are collected by filtration, washed with diethyl ether, and dried under reduced pressure at 25° C. for 17 hours to give (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt (885 mg).

Aufarbeitung

  1. additionfurther added
  2. stirringthe mixture is stirred at 25° C. for 15 minutes
  3. stirringfurther stirred at 5° C. for 30 minutes
  4. filtrationThe precipitated crystals are collected by filtration
  5. washwashed with diethyl ether
  6. customdried under reduced pressure at 25° C. for 17 hours

Quellen und Nachweise

ORD-Eintrag
ord-dc42c43e0c094e16916fc0cb4a7f0c50
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587474

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