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Ethyl Acetate → HCID 131728014, Verbindung

HRID 1799764
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1799764
[CH:1]([N:4]([CH:10]([CH3:12])[CH3:11])[C:5](=[O:9])[O:6][CH2:7]Cl)([CH3:3])[CH3:2].[OH:13][C@@H:14]([C@H:16]1[C:35](=[O:36])[N:18]2[C:19]([C:32]([O-:34])=[O:33])=[C:20]([S:22]/[CH:23]=[CH:24]\[C:25]3[S:29][CH:28]=[N:27][C:26]=3[CH2:30][OH:31])[CH2:21][C@H:17]12)[CH3:15].[Na+].C(OCC)(=O)C>CN(C)C(=O)C.[Cl-].[Na+].O>[OH:13][C@@H:14]([C@H:16]1[C:35](=[O:36])[N:18]2[C:19]([C:32]([O:34][CH2:7][O:6][C:5]([N:4]([CH:10]([CH3:12])[CH3:11])[CH:1]([CH3:3])[CH3:2])=[O:9])=[O:33])=[C:20]([S:22]/[CH:23]=[CH:24]\[C:25]3[S:29][CH:28]=[N:27][C:26]=3[CH2:30][OH:31])[CH2:21][C@H:17]12)[CH3:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 85789591HCID 85789591, VerbindungHCID 131728015HCID 131728015, Verbindung

Produkt 1

HCID 131728014HCID 131728014, VerbindungAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 31374DimethylacetamideLösungsmittel
HCID 57417360
Sodium chloride; water
Lösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

Chloromethyl N,N-diisopropylcarbamate (54 mg) and 75 mg of n-tetrabutyl ammonium bromide were added to 2 ml of a solution of 100 mg of sodium (5R,6S)-6-((1R)-1-hydroxyethyl)-2-[[(Z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-carbapen-2-em-3-carboxylate in N,N-dimethylacetamide, and the mixture was stirred at 30° C. for 3.5 hr. Ethyl acetate (10 ml) and 10 ml of semi-saturated brine were added to the reaction solution, followed by separation. The organic layer was washed three times with 10 ml of semi-saturated brine, was dried over anhydrous magnesium sulfate, and was filtered. Ethyl acetate was removed by distillation under the reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:methanol=15:1) to give 108 mg of the title compound.

Aufarbeitung

  1. customfollowed by separation
  2. washThe organic layer was washed three times with 10 ml of semi-saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationwas filtered
  5. customEthyl acetate was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-63c438eb0d1c44d4a20c6b89d8c3a06d
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08344154B2

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